Sodium borohydride → 1-(Isoquinolin-1-yl)ethan-1-ol

HRID 1637755Notes

Reaction equation

HRID 1637755 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131572141-(Isoquinolin-1-yl)ethan-1-one

Product 1

HCID 123379201-(Isoquinolin-1-yl)ethan-1-olYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-Acetyl-isoquinoline (2.0 g, 11.7 mmole) is dissolved in 50 ml methanol in a 100 ml one neck round bottom flask at 0° C. The solution is treated portionwise with sodium borohydride (495 mg, 13.1 mmole) and the reaction mixture is stirred for 1 h at 0° C. The volatiles are removed in vacuo and the residue is partitioned between 1×50 ml 1N sodium hydroxide and 4×25 ml dichloromethane. The combined organics are dried over potassium carbonate and are concentrated in vacuo to a pale oil. The crude material is chromatographed over 100 g silica gel (230-400 mesh), eluting with 15% acetone/hexane, while collecting 22 ml fractions. Fractions 23-37 are combined and concentrated to afford 1.99 g (98%) of 1-(1-hydroxyethyl)-isoquinoline.

Workup

  1. customThe volatiles are removed in vacuo
  2. customthe residue is partitioned between 1×50 ml 1N sodium hydroxide and 4×25 ml dichloromethane
  3. dry with materialThe combined organics are dried over potassium carbonate
  4. concentrationare concentrated in vacuo to a pale oil
  5. customThe crude material is chromatographed over 100 g silica gel (230-400 mesh)
  6. washeluting with 15% acetone/hexane
  7. customwhile collecting 22 ml fractions
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a59bda8bf05643ceaf94bd9098fc1648
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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