(2S,3S)-N-butyl-3-azido-2-hydroxyheptanamide → (2S,3S)-N-butyl-3-amino-2-hydroxyheptanamide

HRID 2053477Notes

Reaction equation

HRID 2053477 reaction equation
[CH2:1]([NH:5][C:6](=[O:17])[C@@H:7]([OH:16])[C@@H:8]([N:13]=[N+]=[N-])[CH2:9][CH2:10][CH2:11][CH3:12])[CH2:2][CH2:3][CH3:4]>[C].[Pd].CO>[CH2:1]([NH:5][C:6](=[O:17])[C@@H:7]([OH:16])[C@@H:8]([NH2:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 59655565(2S,3S)-N-butyl-3-azido-2-hydroxyheptanamide

Product 1

HCID 59655570(2S,3S)-N-butyl-3-amino-2-hydroxyheptanamideYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To 30 ml of a methanol solution containing 304 mg (1.25 mmol) of (2S,3S)-N-butyl-3-azido-2-hydroxyheptanamide was added 30 mg of 5% palladium carbon, and the resulting mixture was stirred under hydrogen atmosphere for 18 hours. Insoluble materials were filtered off, and the filtrate was distilled under reduced pressure to obtain 254 mg (Yield: 94%) of the title compound.

Workup

  1. filtrationInsoluble materials were filtered off
  2. distillationthe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-54eeba36932747d3ab2e8e016b11c279
Source dataset
uspto-grants-2008_02
Patent number
US07326799B2

Reaction notes

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