Hydrochloric Acid → 1,1-Dimethylethyl N-[(1S)-1-(3-fluorophenyl)-3-oxopropyl]carbamate

HRID 970082Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C@H:19]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)[CH2:20][C:21](OC)=[O:22])=[O:17])([CH3:14])([CH3:13])[CH3:12].CO.Cl>ClCCl>[F:31][C:27]1[CH:26]=[C:25]([C@@H:19]([NH:18][C:16](=[O:17])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:20][CH:21]=[O:22])[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Diisobutylaluminium hydride (1 M in dichloromethane, 39 ml, 39 mmol) was cooled to −78° C. and added dropwise to a solution of methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluorophenyl)propanoate (WO0039125, p60, preparation 12) (5.4 g, 18.2 mmol) in dichloromethane (100 ml) at −78° C. The reaction was stirred for 30 minutes at −78° C., then methanol (50 ml, pre-cooled to −78° C.) was added. The reaction was stirred for 30 minutes, then 2 N hydrochloric acid (250 ml) added. The bi-phasic mixture was allowed to warm up to room temperature, the layers were separated, and the organic layer was dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound as a clear, colourless oil, 4.8 g.

Workup

stirringThe reaction was stirred for 30 minutes
temperatureto warm up to room temperature
customthe layers were separated
dry with materialthe organic layer was dried (MgSO4)
filtrationfiltered
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-bb55a36732114a2baa7dc6c3750f5c9e
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07309790B2

Reaction notes

Loading…