(2S,3S)-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-azido-2-hydroxyheptanamide → (2S,3S)-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-amino-2-hydroxyheptanamide

HRID 2053469Notes

Reaction equation

HRID 2053469 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=[O:20])[C@@H:10]([OH:19])[C@@H:11]([N:16]=[N+]=[N-])[CH2:12][CH2:13][CH2:14][CH3:15]>[C].[Pd].CO>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=[O:20])[C@@H:10]([OH:19])[C@@H:11]([NH2:16])[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 59655568(2S,3S)-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-azido-2-hydroxyheptanamide

Product 1

HCID 59655560(2S,3S)-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-amino-2-hydroxyheptanamideYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To 30 ml of a methanol solution containing 1.45 g (5 mmol) of (2S,3S)-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-azido-2-hydroxyheptanamide was added 150 mg of 5% palladium carbon, and the resulting mixture was stirred under hydrogen atmosphere for 18 hours. Insoluble material was filtered off, and the filtrate was distilled under reduced pressure to obtain 1.18 g (Yield: 91%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-3a7077a6a3e94252be36b171f6187873
Source dataset
uspto-grants-2008_02
Patent number
US07326799B2

Reaction notes

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