(+/-)-cis-4-Benzyloxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester → Tert-butyl cis-4-amino-3-hydroxy-piperidine-1-carboxylate

HRID 402088Notes

Reaction equation

HRID 402088 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14]C(OCC2C=CC=CC=2)=O)[C@H:10]([OH:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[C@H:10]([OH:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86657840(+/-)-cis-4-Benzyloxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86657841Tert-butyl cis-4-amino-3-hydroxy-piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (±)-cis-4-benzyloxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.365 mmol, 0.128 g)) in methanol (3 mL) was added 10% palladium on carbon (0.07 g, wet). The resultant reaction mixture was subjected to hydrogenation using a balloon full of hydrogen for 2 h. The catalyst was filtered through a pad of celite. The pad was washed with methanol (10 mL), and the combined filtrate was concentrated under reduced pressure to get (±)-cis-4-amino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe resultant reaction mixture
  2. customfor 2 h
  3. filtrationThe catalyst was filtered through a pad of celite
  4. washThe pad was washed with methanol (10 mL)
  5. concentrationthe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cedbdd01298e440f837f73f2f0fd3d1a
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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