(3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester → rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

HRID 1670628Notes

Reaction equation

HRID 1670628 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([N:14]=[N+]=[N-])[C@H:10]([OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH2:14])[C@H:10]([OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58745530(3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 10727458rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylateYield 108%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve racemic trans-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.23 mol, 56.6 g) in methanol (500 mL), add 10% palladium on carbon (12.0 g) and hydrogenate (1 atm) at room temperature for 16 h. Filter off the catalyst through a plug of diatomaceous earth and concentrate the filtrate to obtain the title compound (53.7 g, 99%) as a thick, light yellow oil.

Workup

  1. filtrationFilter off the catalyst through a plug of diatomaceous earth
  2. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-76f03226eaf449279fef7c232290bf77
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

Loading…