HCID 58246862, compound → HCID 59382947, compound

HRID 2355332Notes

Reaction equation

HRID 2355332 reaction equation
[N:1]([C@@H:4]([CH3:21])[C@@H:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]([CH3:21])[C@@H:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 58246862HCID 58246862, compound

Product 1

HCID 59382947HCID 59382947, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl (2S,3S)-3-azido-1-cyclohexylbutan-2-ylcarbamate (0.215 g, 0.73 mmol) in methanol (10 mL) was added to wetted Pd/C (0.1 g) and was hydrogenated with a balloon overnight. The reaction mixture was filtered through a pad of Celite and the solvent was removed to give tert-butyl (2S,3S)-3-amino-1-cyclohexylbutan-2-ylcarbamate (0.153 g, 78%), which was used in the next step without purification.

Workup

  1. customwas hydrogenated with a balloon overnight
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-8165e6d2d988458290e81cbc0792dbda
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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