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

HRID 2212561노트

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HRID 2212561 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-44d9b2ca2abf4fc790c30d7862dcdfc3
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07102008B2

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