Lawesson's reagent → (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(5-methyl-1,3-thiazol-2-yl)piperidine

HRID 397639Notes

Reaction equation

HRID 397639 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]([NH:19][CH2:20][C:21](=O)[CH3:22])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>>[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]2[S:33][C:21]([CH3:22])=[CH:20][N:19]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 57063766(2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-oxopropyl)-2-piperidinecarboxamide

Product 1

HCID 57193110(2S)-1-[(4-fluorophenyl)sulfonyl]-2-(5-methyl-1,3-thiazol-2-yl)piperidine

Procedure

The title compound was prepared by a similar method to Example 29 from (2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-oxopropyl)-2-piperidinecarboxamide [see Preparation 81] and Lawesson's reagent. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 75:25, by volume, hexane:ethyl acetate, in 5% increments, to afford (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(5-methyl-1,3-thiazol-2-yl)piperidine as a white solid.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 75:25, by volume, hexane

Sources & evidence

ORD record
ord-e17cfcf8d4e349b9a1c34dddc09c58a9
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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