Benzyl Bromide → (2S)-2-(1-benzyl-1H-1,2,4-triazol-3-yl)-1-[(4-fluorophenyl)sulfonyl]piperidine

HRID 397635Notes

Reaction equation

[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]2[C:25]2[N:29]=[CH:28][NH:27][N:26]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([N:27]1[CH:28]=[N:29][C:25]([C@@H:20]2[CH2:21][CH2:22][CH2:23][CH2:24][N:19]2[S:16]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)(=[O:17])=[O:18])=[N:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Benzyl bromide (40 μl) was added to a solution of (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(1H-1,2,4-triazol-3-yl)piperidine (95 mg) [see Preparation 42] and potassium carbonate (47 mg) in dimethylformamide (5 ml). The reaction mixture was stirred at 50° C. for 7 hours, after which time the solvent was removed under reduced pressure and the residue diluted with ethyl acetate. The organic solution was washed with water, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with 100:0 changing to 50:50, by volume, hexane:ethyl acetate (in 10% increments), to afford (2S)-2-(1-benzyl-1H-1,2,4-triazol-3-yl)-1-[(4-fluorophenyl)sulfonyl]piperidine (35 mg) as a white solid.

Workup

customafter which time the solvent was removed under reduced pressure
additionthe residue diluted with ethyl acetate
washThe organic solution was washed with water
dry with materialdried over magnesium sulphate
customthe solvent removed under reduced pressure
customThe crude product was purified by column chromatography on silica gel eluting with 100:0 changing to 50:50, by volume, hexane

Sources & evidence

ORD record: ord-efc57f09127740b395f2744c18aa8300
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610707B1

Reaction notes

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