Tetrahydrofuran → 1-(4-Fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one
Reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:25]1([S:31](OC)=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C[O:38]CC1>>[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH:9]([S:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:32])[C:8]2=[O:38])=[CH:4][CH:3]=1Participants
5
Conditions
- Temperature
- -20 °C
Procedure
To a cooled (−20° C.) solution of 1-(4-fluorobenzyl)piperidine (17 g, 82 mmol) in anhydrous THF (200 mL) was added LiHMDS (1.0M in THF, 180 mL, 180 mmol) over a period of 15 min. The reaction mixture was stirred for 30 min at −20° C., then methyl phenylsulfinate (15 g, 98 mmol) was added over a period of 5 min. After being stirred at −20° C. for 1 hour, the reaction was quenched by the addition of water (100 mL). EtOAc (200 mL) was added and the organic layer was separated and washed with water (3×100 mL) and brine. The organic layer was dried over Mg2SO4, filtered, concentrated under vacuum. The crude product was used without purification in the next step.
Workup
- stirringAfter being stirred at −20° C. for 1 hour
- customthe reaction was quenched by the addition of water (100 mL)
- additionEtOAc (200 mL) was added
- customthe organic layer was separated
- washwashed with water (3×100 mL) and brine
- dry with materialThe organic layer was dried over Mg2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe crude product was used without purification in the next step
Sources & evidence
- ORD record
- ord-57b731d6cb824b53ba54f426ed48bf91
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07619086B2
Reaction notes
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