Ethanol → 1-Isopropylpiperidin-4-ol
Reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)([CH3:3])[CH3:2].[BH4-].[Na+].C([OH:15])C>>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([OH:15])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]Participants
Procedure
To a cold (0° C.) solution of 1-isopropylpiperidone (purchased at Chemie Brunschwig AG, 100 g, 1.0 eq.) in ethanol (500 mL) was added sodium borohydride (19.3 g, 0.7 eq.) in small portions. The reaction mixture was allowed to warm up to room temperature and was stirred overnight. After concentration in vacuo, ice water (1 kg), sodium hydroxide aqueous solution (28% in mass, 0.5 L) and dichloromethane (1 L) were added. The mixture was stirred vigorously for 4 h and the aqueous layer was extracted with dichloromethane. Combined organic layers were washed with brine, dried over sodium sulfate, filtered and purified by fractionated vacuum distillation (20 mBar). One fraction (95° C. at 20 mBar) was isolated to yield 61.3 g (60%) of the title product as colorless oil. MS (m/e): 144.5 (MH+, 100%).
Workup
- concentrationAfter concentration in vacuo, ice water (1 kg), sodium hydroxide aqueous solution (28% in mass, 0.5 L) and dichloromethane (1 L)
- additionwere added
- stirringThe mixture was stirred vigorously for 4 h
- extractionthe aqueous layer was extracted with dichloromethane
- washCombined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- distillationpurified by fractionated vacuum distillation (20 mBar)
- customOne fraction (95° C. at 20 mBar) was isolated
Sources & evidence
- ORD record
- ord-5718f4785df244e8810f5468f6b4af69
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538101B2
Reaction notes
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