Dichloromethane → tert-Butyl (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate

HRID 1426370Notes

Reaction equation

HRID 1426370 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]2[CH2:14][OH:15])=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+].ClCCl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][N:11]([C:16]([O:17][C:5]([CH3:8])([CH3:6])[CH3:4])=[O:19])[CH2:10][C@H:9]2[CH2:14][OH:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 10340Sodium CarbonateHCID 9855829(3S,4R)-4-(4-Fluorophenyl)-3-piperidinemethanol

Product 1

HCID 10018204tert-Butyl (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylateYield 184.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of [(3S,4R)-4-(4-fluorophenyl)piperidine-3-yl]methanol (3.0 g, 14 mmol), sodium carbonate (6.1 g, 57 mmol), dichloromethane (40 mL) and water (40 mL) was added di-tert-butyl Bicarbonate (3.8 g, 17 mmol) under ice cooling, followed by stirring at the same temperature for 30 minutes. The reaction mixture was added to a mixed solution of dichloromethane and water, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1) to give the title compound (4.0 g, 90% yield).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1)

Sources & evidence

ORD record
ord-0eb7680ef5ee43f08cff9804d6073cc4
Source dataset
uspto-grants-2015_01
Patent number
US08933100B2

Reaction notes

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