Tetrahydrofuran → 1-(4-Fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one

HRID 1817291Notes

Reaction equation

HRID 1817291 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.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[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]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 2733832Lithium HexamethyldisilazideHCID 2759784Methyl benzenesulfinateHCID 43637561-(4-Fluorobenzyl)piperidine

Product 1

HCID 690624651-(4-Fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one

Procedure

To a cooled (0° C.) solution of 1-(4-fluorobenzyl)piperidine (5.0 g, 24.1 mmol) in anhydrous THF (100 mL) was added lithium bis(trimethylsilyl)amide (1.0 M in THF, 53 mL, 53 mmol) dropwise, and the solution was stirred for one half hour. The solution was treated with methyl benzene sulfinate (5.65 g, 36.1 mmol) in anhydrous THF (3 mL) dropwise. After 30 minutes at 0° C., the resultant mixture was quenched with water and partitioned between 10% KHSO4 and CHCl3, the layers separated and the aqueous extracted several more times with CHCl3. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to afford 1-(4-fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one as a waxy solid that was taken on to the next step. ES MS M+1=332

Workup

  1. customthe resultant mixture was quenched with water
  2. custompartitioned between 10% KHSO4 and CHCl3
  3. customthe layers separated
  4. extractionThe organic extract
  5. dry with materialwas dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6bb1a856481c4455abf77ecb762da271
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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