Cesium fluoride → HCID 86672013, compound

HRID 473828Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][C@@H:13]([CH2:15]OS(C)(=O)=O)[CH2:12][CH2:11][N:10]2[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH:5]=[CH:6][C:7]=1[F:8].[F-:31].[Cs+]>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][C@@H:13]([CH2:15][F:31])[CH2:12][CH2:11][N:10]2[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (±)-phenylmethyl (2R,4S)-2-(3,4-difluorophenyl)-4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (200 mg, 0.46 mmol), and cesium fluoride (190 mg, 1.3 mmol) in dimethyl sulfoxide (2 mL) was stirred at 100° C. for 18 hours. The reaction mixture was cooled and purified directly by silica gel chromatography (5% to 25% ethyl acetate in hexanes gradient) to give (±)-phenylmethyl (2R,4S)-2-(3,4-difluorophenyl)-4-(fluoromethyl)piperidine-1-carboxylate (85 mg, 51% yield). MS (EI) for C20H20F3NO2: 364 (MH+).

Workup

temperatureThe reaction mixture was cooled
custompurified directly by silica gel chromatography (5% to 25% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record: ord-d3ba5ca943964d2d8d51c863387989b8
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637499B2

Reaction notes

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