HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → [(3S)-1'-(4-fluorophenyl)hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | (R)-tert-Butyl (2-oxoazepan-3-yl)carbamate | HCID 2756761 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | [(3S)-1'-(4-fluorophenyl)hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl ester | HCID 86591810 | 39.1% |
Reaction Steps
The mixture of [(3R)-hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl ester 400 mg), 4-fluorophenylboronic acid (200 mg), Et3N (0.3 mL), and CuI (150 mg) in CH2Cl2 (5 mL) are mixture at rt for 4 days. The reaction mixture was diluted with brine, extracted with EtOAc, and dried. Concentration followed by flash chromatograph afforded the product (180 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07220856B2 |
| Source dataset | uspto-grants-2007_05 |
| ORD ID | ord-c1a61f053de9436da73890dae0be373c |
| Source note | uspto-grants-2007_05 |