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

HRID 1698437Notes

Reaction equation

HRID 1698437 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-fc673ca78c4f406ab2cf49eddd104304
Source dataset
uspto-grants-2012_04
Patent number
US08163943B2

Reaction notes

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