Lithium borohydride → (4,4-Difluorocyclohexyl)methanamine
Reaction equation
[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8]([NH2:10])=O)[CH2:4][CH2:3]1.[Li+].[BH4-]>C1COCC1>[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([CH2:8][NH2:10])[CH2:4][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of compound 4,4-difluorocyclohexanecarboxamide (1.8 g, 13 mmol) in 100 mL THF was added LiBH4 (1.1 g, 50 mmol) under N2 stirred for overnight. Then the reaction mixture was refluxed for 4 h. After cooled to r.t, it was poured into ice-water slowly. After filtration, the product was extracted with DCM from filtrate. Combined organic layers washed with water, brine, dried over Na2SO4, filtered and condensed to afford compound (4,4-difluorocyclohexyl)methanamine (0.8 g, crude) as a colorless oil.
Workup
- temperatureThen the reaction mixture was refluxed for 4 h
- temperatureAfter cooled
- filtrationAfter filtration
- extractionthe product was extracted with DCM from filtrate
- washCombined organic layers washed with water, brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customcondensed
Sources & evidence
- ORD record
- ord-e9cb286bbe8741b082d6959c1e7115d3
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09416132B2
Reaction notes
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