Sodium borohydride → 1-(Isoquinolin-8-yl)ethan-1-ol
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11](=[O:13])[CH3:12])[CH:4]=[CH:3][N:2]=1.[BH4-].[Na+]>CCO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH:11]([OH:13])[CH3:12])[CH:4]=[CH:3][N:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-(isoquinolin-8-yl)ethanone (0.64 g, 3.74 mmol) in EtOH (37 mL) was added with sodium borohydride (2.26 g, 59.8 mmol). The reaction mixture was stirred overnight. The reaction mixture was quenched with 1M NaOH and extracted with DCM. Purified by normal phase chromatography (10-60% EtOAc in hexane) to yield 1-(isoquinolin-8-yl)ethanol as an oil. Chiral separation (ChiralPak AD-H) provided (S)-1-(isoquinolin-8-yl)ethanol and (R)-1-(isoquinolin-8-yl)ethanol.
Workup
- customThe reaction mixture was quenched with 1M NaOH
- extractionextracted with DCM
- customPurified by normal phase chromatography (10-60% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-8368ae2540fb4ea99bdb01974583b9eb
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273040B2
Reaction notes
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