HCID 67156334, compound → HCID 67151537, compound

HRID 1805252Notes

Reaction equation

HRID 1805252 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:18][OH:19])/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pt]>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:18][OH:19])[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67156334HCID 67156334, compound

Product 1

HCID 67151537HCID 67151537, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [(E)-(S)-3-(4-bromo-phenyl)-1-hydroxymethyl-allyl]-carbamic acid tert-butyl ester (14.7 g) in methanol (150 ml) was added 10% Pt/C (1.68 g) and the resulting mixture was stirred under a H2 balloon at room temperature for 3 hours (whereby the reaction progress was checked continuously by 1H NMR). The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to afford [(S)-3-(4-bromo-phenyl)-1-hydroxymethyl-propyl]-carbamic acid tert-butyl ester as a yellow solid (11.5 g, 78%). MS (ISP): 346.0 ([{81Br}M+H]+), 344.0 ([{79Br} M+H]+), 289.9 ([{81Br}M+H—C4H8]+), 288.0 ([{79Br} M+H—C4H8]+), 246.1 ([{81Br}M+H—C4H8—CO2]+), 244.1 ([{79Br} M+H—C4H8—CO2]+).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1fc1691456484b058ea095b545235229
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

Loading…