HCID 68883845, compound → HCID 68884356, compound

HRID 1269515Notes

Reaction equation

HRID 1269515 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([C:21]([O:23]CC3C=CC=CC=3)=[O:22])([CH3:20])[CH3:19])[CH:12]=2)[CH2:6]1)=[O:4]>[Pd].CO>[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([C:21]([OH:23])=[O:22])([CH3:20])[CH3:19])[CH:12]=2)[CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 68883845HCID 68883845, compound

Product 1

HCID 68884356HCID 68884356, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (18 mg, 10 wt %) was added to a solution of (S)-3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid methyl ester (90 mg, 0.22 mmol) in methanol (3 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 65 mg (92%) of (S)-3-[3-(1-carboxy-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid methyl 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-256b3fbf40254d78a8b827a06e5b4ba7
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

Loading…