{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-38cadda2a33648a9ad5bbd9f93ac95f2","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"8a4515c86cba6aa21fd128bef9719272ec0071bd274998951c1c3af8ffe6dfd3","doi":"10.1002/anie.201409186","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-e1a37b4fe2e07de6","route_slugs":["ord-38cadda2a33648a9ad5bbd9f93ac95f2-ea1b1f5a034e"],"reactant_slugs":["ord-compound-38c8935dd5e9e5779ec7"],"product_slugs":["ord-compound-fdea04b0fee0de42140f"],"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":"lit_pub_bo_787"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1CC1)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"540792-73-2"}],"amount":{"moles":{"value":1.6,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C[OH2+].C[OH2+].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ir].[Ir]"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"12148-71-9"}],"amount":{"moles":{"value":0.04,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C(=CC=C2C=CC=3C=CC(=NC3C12)C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"484-11-7"}],"amount":{"moles":{"value":0.08,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"73183-34-3"}],"amount":{"moles":{"value":0.8,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C1CCCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"110-82-7"}],"amount":{"volume":{"value":3.000002,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":70,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"notes":{"procedure_details":"A mixture of 3,4,7,8-tetramethyl-1,10-phenanthroline (46.9 mg, 71 µmol) and [Ir(OMe)(cod)]2 (33.5 mg, 0.14 mmol) in cyclohexane (5 mL) was stirred at room temperature for 15 min in a Schlenk flask under N2 atmosphere. N-Cyclopropylpivalamide (1a: 2.0 g, 14 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin: 3.08 mL, 21 mmol) and cyclohexane (20 mL) were added to the mixture under N2 flow. Then, the reaction mixture was heated at 80 °C for 18 h under N2 atmosphere. The reaction mixture was concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography (chloroform/acetone = 25:1 to 20:1). The collected fractions were purified again by silica gel column chromatography (hexane/ether = 1:2 to 1:4) to give 2.33 g of the product 2a as a white solid in a 62% yield. NOE was observed between H1 and H2 . This result indicates that boronate 2a has cis configuration."},"outcomes":[{"reaction_time":{"value":18,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1CC1B2OC(C)(C)C(O2)(C)C)C(C)(C)C"},{"type":"CAS_NUMBER","value":"1807546-49-1"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":6}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (600 MHz, CDCl3) δ 6.58 (brs, 1H, NH), 3.50-3.45 (m, 1H, 1-H), 1.27 (s, 6H, pinacol methyl), 1.25 (s, 6H, pinacol methyl), 1.18 (s, 9H, tBu), 1.10 (ddd, J= 10.8, 6.6, 4.2 Hz, 1H, 3-Ha), 0.56 (dt, J= 7.8, 4.8 Hz, 1H, 3-Hb), 0.24 (dt, J= 10.8, 7.8 Hz, 1H, 2-H).; 13C NMR (150 MHz, CDCl3) δ 179.0 (CO), 83.5 (C(CH3)2), 38.6 (C(CH3)3), 28.3 (C-1), 27.4 (C(CH3)3), 25.0 (C(CH3)2), 24.5 (C(CH3)2), 12.7 (C-3), - 1.2 (br, C-2).;"}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 268.2066","data":{"found":{"float_value":268.2066,"description":"Observed m/z"}}},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1002/anie.201409186"}}},"entities":[{"slug":"ord-compound-38c8935dd5e9e5779ec7","name":"C8H15NO · ORD OWXPHZLYDIDNFZ-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)NC1CC1","inchi":"InChI=1S/C8H15NO/c1-8(2,3)7(10)9-6-4-5-6/h6H,4-5H2,1-3H3,(H,9,10)","formula":"C8H15NO"},{"slug":"ord-compound-fdea04b0fee0de42140f","name":"C14H26BNO3 · ORD MGDVJAOPVFEGKV-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)NC1CC1B1OC(C)(C)C(C)(C)O1","inchi":"InChI=1S/C14H26BNO3/c1-12(2,3)11(17)16-10-8-9(10)15-18-13(4,5)14(6,7)19-15/h9-10H,8H2,1-7H3,(H,16,17)","formula":"C14H26BNO3"}],"dataset":{"dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","name":"Borylation dataset from Roche","description":"Borylation 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":1111,"path":"data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","sha256":"e01a389cac3e6cce5746ef54dbe6b8d3040d764f987b1fc13790f5aeff5598fa","bytes":210626,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet"},"publication":{"slug":"ord-publication-e1a37b4fe2e07de6","title":"Literature experiment — 10.1002/anie.201409186","source_type":"paper","doi":"10.1002/anie.201409186","url":"https://doi.org/10.1002/anie.201409186","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"]}