Methanol → methyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylate

HRID 397670Notes

Reaction equation

HRID 397670 reaction equation
CO.Cl.[CH3:4]N(C)CCCN=C=NCC.[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]2[C:31]([OH:33])=[O:32])(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C1C=CN=CC=1.ClCCl>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]2[C:31]([O:33][CH3:4])=[O:32])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 768662(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57268970methyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylateYield 79.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-Dimethylaminopyridine (61 mg), methanol (45 μl) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (192 mg) were added to a solution of (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acid (287 mg) [see Preparation 38] in dichloromethane (6 ml). The reaction mixture was stirred at room temperature for 56 hours after which time it was diluted with dichloromethane and washed with 1N aqueous hydrochloric acid solution followed by saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 50:50, by volume, hexane:ethyl acetate, to afford methyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylate (239 mg) as an oil.

Workup

  1. washwashed with 1N aqueous hydrochloric acid solution
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 50:50, by volume, hexane

Sources & evidence

ORD record
ord-9a4492d48a8047608dbd2a1c2e630d4f
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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