Dichloromethane → 1,1-dimethylethyl [(3S)-1-methyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate

HRID 1366443Notes

Reaction equation

HRID 1366443 reaction equation
[CH2:1]([NH:4][C:5]([C@@H:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8][CH:9]=[CH2:10])=[O:6])C=C.[CH2:19](Cl)Cl>>[CH3:19][N:4]1[CH2:1][CH:10]=[CH:9][CH2:8][C@H:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:5]1=[O:6]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 866369391,1-dimethylethyl {(1S)-1-[(2-propen-1-ylamino)carbonyl]-3-buten-1-yl}carbamate

Product 1

HCID 866369401,1-dimethylethyl [(3S)-1-methyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamateYield 63%

Conditions

Temperature
40 °C

Procedure

1,1-Dimethylethyl {(1S)-1-[(2-propen-1-ylamino)carbonyl]-3-buten-1-yl}carbamate (0.94 g, 3.9 mmol) was dissolved in DCM (350 mL) and 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium (0.3 g, 3.5 mmol) was added. The resulting solution was heated to 40° C. and stirred for 12 hours. The solvent was evaporated under reduced pressure and the crude product was purified by RP-HPLC yielding 1,1-dimethylethyl [(3S)-1-methyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate (0.6 g, 63%). LCMS: (M+H)+: 242.3.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-461ecdcd3467406c9edd051fc270edfd
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…