Sodium borohydride → alpha-Methylisoquinoline-3-methanol

HRID 1637750

Reaction equation

HRID 1637750 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 112752751-(Isoquinolin-3-yl)ethan-1-one

Product 1

HCID 18799682alpha-Methylisoquinoline-3-methanolYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Acetyl-isoquinoline (1.53 g, 8.9 mmole) is dissolved in 42 ml methanol in a 100 ml one neck round bottom flask at 0° C. The solution is treated portionwise with sodium borohydride (388 mg, 10.3 mmole) and the reaction mixture is stirred 30 min at 0° C. The volatiles are removed in vacuo and the residue is partitioned between 1×100 ml 1N sodium hydroxide and 3×25 ml dichloromethane. The combined organics are dried over potassium carbonate and are concentrated in vacuo to a pale yellow solid. The crude material is chromatographed over 60 g silica gel (230-400 mesh), eluting with 40% acetone/hexane, while collecting 9 ml fractions. Fractions 26-45 are combined and concentrated to afford 1.23 g (80%) of 3-(1-hydroxyethyl)-isoquinoline.

Workup

  1. customThe volatiles are removed in vacuo
  2. customthe residue is partitioned between 1×100 ml 1N sodium hydroxide and 3×25 ml dichloromethane
  3. dry with materialThe combined organics are dried over potassium carbonate
  4. concentrationare concentrated in vacuo to a pale yellow solid
  5. customThe crude material is chromatographed over 60 g silica gel (230-400 mesh)
  6. washeluting with 40% acetone/hexane
  7. customwhile collecting 9 ml fractions
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-55e7e01a2262485a807e4d02438b7ea1
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Linked notes

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