(2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-azido-2-hydroxyheptanamide → (2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-amino-2-hydroxyheptanamide

HRID 1698434Notes

Reaction equation

HRID 1698434 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][C:11](=[O:22])[C@@H:12]([OH:21])[C@@H:13]([N:18]=[N+]=[N-])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=2[O:2]1>[C].[Pd].CO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][C:11](=[O:22])[C@@H:12]([OH:21])[C@@H:13]([NH2:18])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 1

HCID 59655561(2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-azido-2-hydroxyheptanamide

Product 1

HCID 59655569(2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-amino-2-hydroxyheptanamideYield 95.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To 30 ml of a methanol solution containing 395 mg (1.29 mmol) of (2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-azido-2-hydroxyheptanamide was added 40 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 344 mg (Yield: 95%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-d14dedb4db8e43e19ed049d5b32575a7
Source dataset
uspto-grants-2012_04
Patent number
US08163943B2

Reaction notes

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