HCID 10657786, compound → rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

HRID 2208144Notes

Reaction equation

HRID 2208144 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C@@H:5]1[OH:17])=[N+]=[N-].[H][H]>CO.[OH-].[Pd+2].[OH-]>[NH2:1][C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:6][C@H:5]1[OH:17]

Participants

5

Reactant 2

HCID 10657786HCID 10657786, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10727458rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(3S*,4S*)-tert-butyl 4-azido-3-hydroxypiperidine-1-carboxylate from example C1 (47 g, 194 mmol) is dissolved in methanol (1200 mL) under nitrogen. Palladium hydroxide (20% on carbon; 4.7 g) is added. The atmosphere is changed to hydrogen and the stirred reaction mixture is hydrogenated at room temperature and 70 psi for 72 hours. The mixture is filtered through celite. The filtrate is evaporated. The residue is recrystallized from CH2Cl2 with a small amount of MeOH to obtain the title compound as a white solid.

Workup

  1. customthe stirred reaction mixture
  2. customis hydrogenated at room temperature
  3. filtrationThe mixture is filtered through celite
  4. customThe filtrate is evaporated
  5. customThe residue is recrystallized from CH2Cl2 with a small amount of MeOH

Sources & evidence

ORD record
ord-770630fa8ecc403aa746623adc804050
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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