Triethylamine → (2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-oxopropyl)-2-piperidinecarboxamide

HRID 397690Notes

Reaction equation

HRID 397690 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]2[C:39]([NH:41][CH2:42][CH:43]([OH:45])[CH3:44])=[O:40])(=[O:32])=[O:31])=[CH:26][CH:25]=1.C(N(CC)CC)C>ClCCl>[F:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]2[C:39]([NH:41][CH2:42][C:43](=[O:45])[CH3:44])=[O:40])(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 159087TriacetoxyperiodinaneHCID 57047664(2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-hydroxypropyl)-2-piperidinecarboxamide

Product 1

HCID 57063766(2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-oxopropyl)-2-piperidinecarboxamideYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent (814 mg) was added to a stirred solution of (2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-hydroxypropyl)-2-piperidinecarboxamide (548 mg) [see Preparation 80) and triethylamine (0.89 ml) in dichloromethane (20 ml). The reaction mixture was stirred for 1 hr after which time the mixture was filtered through a pad of basic alumina and washed through with dichloromethane to afford (2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-oxopropyl)-2-piperidinecarboxamide (300 mg).

Workup

  1. filtrationwas filtered through a pad of basic alumina
  2. washwashed through with dichloromethane

Sources & evidence

ORD record
ord-abec624247d342298502eb9bb7101357
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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