Water → HCID 59506262, compound

HRID 1098759Notes

Reaction equation

HRID 1098759 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([OH:16])[CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:17][C:18]([C:20]1[CH:25]=[CH:24][C:23](F)=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=1)=[O:19].O>CS(C)=O.ClCCl>[C:6]([O:5][C:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([O:16][C:23]2[CH:24]=[CH:25][C:20]([C:18](=[O:19])[CH3:17])=[CH:21][C:22]=2[C:27]([F:28])([F:29])[F:30])[CH2:11]1)=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5456991-Boc-3-hydroxypiperidineHCID 6056784'-Fluoro-3'-(trifluoromethyl)acetophenone

Product 1

HCID 59506262HCID 59506262, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of sodium hydride (408 mg, 10.2 mmol) in DMSO (15 ml) was added 1-boc-3-hydroxypiperidine (2.00 g, 10.2 mmol) at 0° C. Stirring was continued for 30 min at 10° C. and 4-fluoro-3-(trifluormethyl)acetophenone (1.40 g, 6.79 mmol) was added dropwise. The reaction mixture was stirred at RT for 1 h and then transferred into water (200 ml) at 0° C. Dichloromethane (300 ml) was added. The organic phase was washed with water (200 ml) and dried over sodium sulfate. Evaporation and purification of the crude product by silica gel chromatography using ethyl acetate/heptane=1:1 gave the desired product (1.80 g, 68%).

Workup

  1. stirringThe reaction mixture was stirred at RT for 1 h
  2. washThe organic phase was washed with water (200 ml)
  3. dry with materialdried over sodium sulfate
  4. customEvaporation and purification of the crude product by silica gel chromatography

Sources & evidence

ORD record
ord-761f47309743404786f2590f888dd2a1
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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