{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-89c7d517418648fd92734995b148b41b","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"bfd1f133c12ae734e44576e19a1c4f1d6d12f8dff28fe614a3a4f0900e9f4f55","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-89c7d517418648fd92734995b148b41b-eb44e9a5734c","ord-89c7d517418648fd92734995b148b41b-38c9a269c345"],"reactant_slugs":["ord-compound-4be0354ebbfc7e1b79e1","ord-compound-7a5ea1f0381bb40c0ab8"],"product_slugs":["ord-compound-b7996aa2f9c1cf977667"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lsf_lit_minisci_124"},{"type":"CUSTOM","details":"rxn_tech from SURF table","value":"alkylation"},{"type":"REACTION_TYPE","details":"alkylation minisci","value":"alkylation minisci"}],"inputs":{"additive_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(=O)(O)O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7664-93-9"}],"amount":{"moles":{"value":2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"IC1COC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"26272-85-5"}],"amount":{"moles":{"value":2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC(=C2C=CC=CC12)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"491-35-0"}],"amount":{"moles":{"value":1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Fe].O=S(=O)(O)O.O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7782-63-0"}],"amount":{"moles":{"value":0.6,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OO"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7722-84-1"}],"amount":{"moles":{"value":6,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7732-18-5"}],"amount":{"volume":{"value":0.6,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"67-68-5"}],"amount":{"volume":{"value":9.4,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}}},"notes":{"procedure_details":"H2O2  (30%  in  H2O;  0.31  mL,  3.0  mmol)  was  added  dropwise  over 1-2 min to a stirred solution of lepidine 1a (132 μL, 1.0 mmol), concentrated H2SO4 (107 μL, 2.0 mmol),  3-iodooxetane  (368  mg,  2.0  mmol)  and  iron(II)  sulfate  heptahydrate  (80  mg,  0.3  mmol)  in  DMSO (10 mL) at room temperature. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg,  0.3  mmol)  was  added  and  the  mixture  was  stirred  at  room  temperature  for  30  min.  Further  H2O2(0.31  mL,  3.0  mmol)  and  iron(II)  sulfate  heptahydrate  (80  mg,  0.3  mmol)  was  added,  and  the  mixture  was  stirred  for  15  min,  then  poured  into  a  0.2  M  solution  of  NaOH  (30  mL)  and  Et2O  (50  mL).  The  aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The  combined  organic  extracts  were  washed  with  brine  (1  x  30  mL),  dried  (MgSO4),  filtered  and  the  solvent  removed  under  vacuum  to  leave  a  crude  oil.  The  oil  was  purified  by  preparative  thin-layer  chromatography  using  EtOAc  /  hexanes  (3:7)  as  eluent  to  give  a  mixture  of  lepidine  1a  and  desired  product 2a  (25  mg),  and  the  desired  product  2a  (82  mg,  40%)  as  a  solid.  An  analytical  portion  of  the  product 2a was recrystallized from EtOAc / hexanes for data purposes"},"outcomes":[{"reaction_time":{"value":0.75,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N=1C=2C=CC=CC2C(=CC1C3COC3)C"},{"type":"CAS_NUMBER","value":"1180653-56-8"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":40}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz; CDCl3) δ - 4 -8.07 (d, J = 8.3 Hz, 1H), 7.97 (d, J = 8.3 Hz, 1H), 7.71 (t, J = 7.6 Hz, 1H), 7.55 (t, J = 7.6 Hz, 1H), 7.38 (s, 1H), 5.19 (dd, J = 8.3, 6.0 Hz, 2H), 5.05 (t, J = 6.3 Hz, 2H), 4.51 (app. quint., J = 7.5 Hz, 1H), 2.73 (s,  3H);  13C  NMR  (100  MHz;  CDCl3) δ  160.6,  147.7,  145.4,  129.8,  129.5,  127.3,  126.2,  123.8,  120.0,  76.9,  42.6,  19.0"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-4be0354ebbfc7e1b79e1","name":"C10H9N · ORD MUDSDYNRBDKLGK-UHFFFAOYSA-N","smiles":"Cc1ccnc2ccccc12","inchi":"InChI=1S/C10H9N/c1-8-6-7-11-10-5-3-2-4-9(8)10/h2-7H,1H3","formula":"C10H9N"},{"slug":"ord-compound-7a5ea1f0381bb40c0ab8","name":"C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N","smiles":"IC1COC1","inchi":"InChI=1S/C3H5IO/c4-3-1-5-2-3/h3H,1-2H2","formula":"C3H5IO"},{"slug":"ord-compound-b7996aa2f9c1cf977667","name":"C13H13NO · ORD YVLUMSNFYVKNMF-UHFFFAOYSA-N","smiles":"Cc1cc(C2COC2)nc2ccccc12","inchi":"InChI=1S/C13H13NO/c1-9-6-13(10-7-15-8-10)14-12-5-3-2-4-11(9)12/h2-6,10H,7-8H2,1H3","formula":"C13H13NO"}],"dataset":{"dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","name":"Minisci dataset from Roche","description":"Minisci reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":130,"path":"data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","sha256":"ebefbe9aba687f182d4f068e94be0f7fd71d1189bdb2eff2aca6fedf4d522bf3","bytes":37643,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet"},"publication":{"slug":"ord-publication-91c8bf15879e5ce2","title":"Literature experiment — 10.1021/jo9010624","source_type":"paper","doi":"10.1021/jo9010624","url":"https://doi.org/10.1021/jo9010624","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}