Sodium borohydride → 3-Hydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid ethyl ester

HRID 2212561ノート

反応式

HRID 2212561 の反応式
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:31])[C:7]([CH3:30])([CH3:29])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[C:20]([CH3:28])[CH:19]=2)=[CH:12][CH:11]=1)=[O:9])[CH3:4]>CO>[CH2:3]([O:5][C:6](=[O:31])[C:7]([CH3:30])([CH3:29])[CH:8]([OH:9])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[C:20]([CH3:28])[CH:19]=2)=[CH:12][CH:11]=1)[CH3:4]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 695965072,2-Dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-3-oxo-propionic acid ethyl ester

生成物 1

HCID 695964293-Hydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid ethyl ester収率 50%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium borohydride (0.021 g, 0.56 mmol) was added to a solution of 2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-3-oxo-propionic acid ethyl ester (0.22 g, 0.56 mmol) in methanol (10 mL) under nitrogen at room temperature. The reaction was stirred for 2 h then was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting hexane:ethyl acetate (50:50, v:v) to give 3-hydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid ethyl ester (0.11 g, 50%) as an oil. MS found: (M+H)+=394.

後処理

  1. customthen was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil
  6. customThe product was purified by FCC on silica gel
  7. washeluting hexane:ethyl acetate (50:50, v:v)

出典と根拠

ORDレコード
ord-44d9b2ca2abf4fc790c30d7862dcdfc3
出典データセット
uspto-grants-2006_09
特許番号
US07102008B2

反応ノート

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