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

HRID 750248ノート

反応式

HRID 750248 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-47b997940c734a09a5b6a568e49d6bd6
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

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