3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid 4-isopropyl-phenyl ester → 3-[3-(1-Carboxy-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid 4-isopropyl-phenyl ester

HRID 1269507Notes

Reaction equation

HRID 1269507 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([C:29]([O:31]CC4C=CC=CC=4)=[O:30])([CH3:28])[CH3:27])[CH:20]=3)[CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>[Pd].CO>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([C:29]([OH:31])=[O:30])([CH3:27])[CH3:28])[CH:20]=3)[CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 688829373-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid 4-isopropyl-phenyl ester

Product 1

HCID 98453233-[3-(1-Carboxy-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid 4-isopropyl-phenyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (180 mg, 10 wt %) was added to a solution of 3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid 4-isopropyl-phenyl ester (1.76 g, 3.41 mmol) in methanol (15 mL) and the resulting mixture hydrogenated at atmospheric pressure for 3 h. The reaction mixture was filtered through a plug of celite and the celite plug washed thoroughly with ethyl acetate. The combined filtrates were concentrated under reduced pressure to provide 1.26 g (87%) of: 3-[3-(1-Carboxy-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid 4-isopropyl-phenyl ester as a clear oil.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washthe celite plug washed thoroughly with ethyl acetate
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-9401ba8d903d42fc92b85fdcbed4ee5f
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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