Methanol → Methyl 4-hydroxypiperidine-4-carboxylate

HRID 712212Notes

Reaction equation

HRID 712212 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([OH:17])([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.[CH3:18]O>[OH-].[Pd+2].[OH-]>[OH:17][C:11]1([C:14]([O:16][CH3:18])=[O:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 887MethanolHCID 203941814-Piperidinecarboxylicacid, 4-hydroxy-1-(phenylmethyl)-

Product 1

HCID 21093366Methyl 4-hydroxypiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

To a stirred solution of 1-benzyl-4-hydroxypiperidine-4-carboxylic acid (1.2 g, 5.1 mmol) in MeOH (15 mL) was added palladium hydroxide and the resulting mixture was stirred at rt for 6 h under H2 atmosphere. After completion (by TLC), the mixture was passed through celite and the filtrate evaporated under reduced pressure. The crude (1 g) residue was carried forward to the next step without further purification. MS: 160.18 [M+H]+.

Workup

  1. customthe filtrate evaporated under reduced pressure
  2. customThe crude (1 g) residue was carried forward to the next step without further purification

Sources & evidence

ORD record
ord-11ecec35c18a44528df52b212433cdca
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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