Oxonium, triethyl-, hexafluorophosphate(1-) (1:1) → ethyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboximidate

HRID 397665Notes

Reaction equation

HRID 397665 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([NH2:19])=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[CH2:27]([O+](CC)CC)[CH3:28]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17](=[NH:19])[O:18][CH2:27][CH3:28])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 167684Oxonium, triethyl-, hexafluorophosphate(1-) (1:1)HCID 8402010(2S)-1-[(4-Fluorophenyl)sulfonyl]-2-piperidinecarboxamide

Product 1

HCID 57097015ethyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboximidateYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2S)-1-[(4-Fluorophenyl)sulfonyl]-2-piperidinecarboxamide (286 mg) [see Preparation 40] was added to a solution of triethyloxonium hexafluorophosphate (304 mg) in dichloromethane (5 ml). The reaction mixture was stirred at room temperature for 18 hours after which time the mixture was diluted with dichloromethane and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried over magnesium sulphate and the solvent was removed under reduced pressure to afford ethyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboximidate (290 mg).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d61357ce9d34439fa98d3b9052b5191a
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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