Sodium borohydride → 58794-07-3

HRID 920229Notes

Reaction equation

HRID 920229 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]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53403113HCID 53403113, compound

Product 1

HCID 8257588258794-07-3

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. customThe reaction mixture was quenched with 1M NaOH
  2. extractionextracted with DCM
  3. 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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