HCID 59201311, compound → HCID 59201539, compound

HRID 451773Notes

Reaction equation

HRID 451773 reaction equation
[N:1]([C@H:4]([CH2:21][CH3:22])[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]([CH2:21][CH3:22])[C@@H:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 59201311HCID 59201311, compound

Product 1

HCID 59201539HCID 59201539, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl (2S,3R)-3-azido-1-cyclohexylpentan-2-ylcarbamate (64 mg, 0.21 mmol) and 10% Pd/C in methanol (20 mL) was hydrogenated at 40 psi for 1 h. The catalyst was filtered off, and the filtrate concentrated to give tert-butyl (2S,3R)-3-amino-1-cyclohexylpentan-2-ylcarbamate (55 mg, 93%). MS ESI +ve m/z 285 (M+H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-7d4639927ca448ddaf9e275e313f4e91
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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