Methanol → HCID 68290013, compound

HRID 878774Notes

Reaction equation

HRID 878774 reaction equation
[CH:1]1([C:5]([F:18])([F:17])[C:6]2[CH:16]=[CH:15][C:9]([C:10](OCC)=[O:11])=[CH:8][CH:7]=2)[CH2:4][CH2:3][CH2:2]1.CO.[BH4-].[Li+].O>O1CCCC1>[CH:1]1([C:5]([F:17])([F:18])[C:6]2[CH:16]=[CH:15][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 69437235Ethyl 4-(cyclobutyldifluoromethyl)benzoate

Product 1

HCID 68290013HCID 68290013, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[cyclobutyl(difluoro)methyl]benzoate (synthesized by the method of WO2005/032465, 140 mg, 0.55 mmol) in tetrahydrofuran (5 mL) and methanol (112 μL, 2.76 mmol) was added lithium borohydride (60 mg, 2.75 mmol) at 0° C. The mixture was stirred at room temperature for 3 hours, and then to the reaction solution was added water at 0° C., and the mixture was extracted with ethyl acetate three times. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give a crude {4-[cyclobutyl(difluoro)methyl]phenyl}methanol (111 mg) as a colorless oil. The resultant was used in the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acbebdb563bf4f3ebf18d0db0d05a71a
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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