tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-(dimethylamino)piperidine-1-carboxylate → tert-Butyl cis(+/-)-4-amino-3-(dimethylamino)piperidine-1-carboxylate

HRID 1425309Notes

Reaction equation

HRID 1425309 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@H:13]1[N:25]([CH3:27])[CH3:26])=O)C1C=CC=CC=1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[NH2:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][C@H:13]1[N:25]([CH3:27])[CH3:26]

Participants

5

Reactant 2

HCID 86648775tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-(dimethylamino)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86648776tert-Butyl cis(+/-)-4-amino-3-(dimethylamino)piperidine-1-carboxylateYield 100.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

20% Palladium hydroxide (15 mg) was added to a solution of tert-butyl cis(±)-4-{[benzyloxy)carbonyl]amino}-3-(dimethylamino)piperidine-1-carboxylate obtained in Example (200b) (144 mg, 0.381 mmol) in methanol (4 mL) at room temperature, and the mixture was stirred in a hydrogen atmosphere at 50° C. for six hours. The insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain 93 mg of the title compound (100%) as a colorless oily substance.

Workup

  1. customThe insoluble matter was separated by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7b281f9757a54fbab899ae1f450baae7
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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