tert-Butyl 4-azido-3-hydroxypiperidine-1-carboxylate → tert-Butyl 4-amino-3-hydroxypiperidine-1-carboxylate

HRID 1392380Notes

Reaction equation

HRID 1392380 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH:5]1[OH:17])=[N+]=[N-]>CO>[NH2:1][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:6][CH:5]1[OH:17]

Participants

3

Reactant 1

HCID 21874176tert-Butyl 4-azido-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 21874161tert-Butyl 4-amino-3-hydroxypiperidine-1-carboxylateYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-azido-3-hydroxypiperidine-1-carboxylate (62 g) obtained in Step 3 was dissolved in 300 ml of methanol. The mixture was hydrogenated with 10%-palladuim at room temperature under 35 psi for about 48 hours and filtered. The resulting filtrate was concentrated to give the titled compound (55 g) as a colorless and oily form.

Workup

  1. filtrationfiltered
  2. concentrationThe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-54c0fe3bbc764a8f9f26f79c02306f69
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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