Methanol → 2-benzyl-6-chloro-4-(4-hydroxymethylphenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750248Notes

Reaction equation

HRID 750248 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4].CO.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 865995582-benzyl-6-chloro-4-(4-formylphenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

Product 1

HCID 691565792-benzyl-6-chloro-4-(4-hydroxymethylphenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-benzyl-6-chloro-4-(4-formylphenyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (66 mg), methanol (1.0 ml) and THF (1.0 ml) was added sodium borohydride (6 mg) at 0° C. with stirring, and the mixture was stirred for 1 hr. The reaction mixture was concentrated, and the residue was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (30 mg) as a colorless powder.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between 1N hydrochloric acid and ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-47b997940c734a09a5b6a568e49d6bd6
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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