Sodium borohydride → HCID 118114009, compound

HRID 2178387Notes

Reaction equation

HRID 2178387 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[C:7](=[O:13])[CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[CH:7]([OH:13])[CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12439091HCID 12439091, compound

Product 1

HCID 118114009HCID 118114009, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred 0° C. solution of 3-methoxy-6,7-dihydroisoquinolin-8(5H)-one (1.90 g, 10.72 mmol) in methanol (30 mL) was added sodium borohydride (1.10 g, 29.08 mmol) in small portions. The resulting mixture was allowed to warm to room temperature. After 2 h, the mixture was quenched with water (20 mL) and was extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over sodium sulfate, filtered, and concentrated. Chromatographic purification of the residue (silica gel, 50% ethyl acetate in petroleum ether elute) afforded 1.60 g (85%) of 3-methoxy-5,6,7,8-tetrahydroisoquinolin-8-ol as a light yellow solid.

Workup

  1. customthe mixture was quenched with water (20 mL)
  2. extractionwas extracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification of the residue (silica gel, 50% ethyl acetate in petroleum ether elute)

Sources & evidence

ORD record
ord-b2165403630f44d8b3c100203b0cccf9
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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