(S)-1-(1,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid benzyl ester → (2S)-1-[(1,1-Dioxido-4-thiomorpholinyl)carbonyl]-2-piperidinecarboxylic acid

HRID 336197Notes

Reaction equation

HRID 336197 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[C:17]([N:19]1[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]1)=[O:18])=[O:10])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[O:26]=[S:22]1(=[O:25])[CH2:21][CH2:20][N:19]([C:17]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]2[C:9]([OH:10])=[O:8])=[O:18])[CH2:24][CH2:23]1

Participants

4

Reactant 1

HCID 58564025(S)-1-(1,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid benzyl ester

Product 1

HCID 58563809(2S)-1-[(1,1-Dioxido-4-thiomorpholinyl)carbonyl]-2-piperidinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1-(1,1-Dioxo-1λ6-thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid benzyl ester (1.53 g; 4.021 mmol) in ethyl acetate (100 mL) is added 10% palladium on carbon (500 mg) and the reaction mixture is placed under an atmosphere of hydrogen and stirred at room temperature overnight. After this time, the mixture is filtered through Celite®. The Celite® is washed with 50% ethyl acetate in ethanol then ethanol and the combined filtrates are concentrated in vacuo to afford the title compound as a white solid, m/z 291 [M+H+].

Workup

  1. filtrationAfter this time, the mixture is filtered through Celite®
  2. washThe Celite® is washed with 50% ethyl acetate in ethanol
  3. concentrationethanol and the combined filtrates are concentrated in vacuo

Sources & evidence

ORD record
ord-ed8df3ce3e6d446c8e5df5de0dbd2072
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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