Triethylamine → [(3S)-1'-(4-fluorophenyl)hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl ester

HRID 1353479Notes

Reaction equation

HRID 1353479 reaction equation
[O:1]=[C:2]1[C@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.CCN(CC)CC>C(Cl)Cl.[Cl-].[Na+].O.[Cu]I>[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:2]2=[O:1])=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 2856454-Fluorophenylboronic acidHCID 2756761(R)-tert-Butyl (2-oxoazepan-3-yl)carbamate

Product 1

HCID 86591810[(3S)-1'-(4-fluorophenyl)hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl esterYield 39.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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).

Workup

  1. customat rt
  2. customfor 4 days
  3. extractionextracted with EtOAc
  4. customdried
  5. concentrationConcentration

Sources & evidence

ORD record
ord-c1a61f053de9436da73890dae0be373c
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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