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

HRID 2105955Notes

Reaction equation

HRID 2105955 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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21225700DiisobutylaluminumhydrideHCID 57318280Methyl (βS)-β-[[(1,1-dimethylethoxy)carbonyl]amino]-3-fluorobenzenepropanoate

Product 1

HCID 590339311,1-Dimethylethyl N-[(1S)-1-(3-fluorophenyl)-3-oxopropyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (WO 0039125) (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

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

Sources & evidence

ORD record
ord-9b41ac6641e343ae9f7f6812f20db698
Source dataset
uspto-grants-2009_08
Patent number
US07579471B2

Reaction notes

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