Sodium triacetoxyborohydride → 2(R)-(3,4-methylenedioxy-benzylamino)-3-methylbutyric acid benzyl ester

HRID 1760801노트

반응식

HRID 1760801 반응식
[CH2:1]([O:8][C:9](=[O:15])[C@@H:10]([CH:12]([CH3:14])[CH3:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](O[C:26](=[O:28])[CH3:27])OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:15])[C@H:10]([NH:11][CH2:14][C:12]1[CH:13]=[CH:27][C:26]2[O:28][CH2:1][O:8][C:9]=2[CH:10]=1)[CH:12]([CH3:13])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 5049666Sodium triacetoxyborohydrideHCID 7350007Benzyl D-valinate

생성물 1

HCID 542486302(R)-(3,4-methylenedioxy-benzylamino)-3-methylbutyric acid benzyl ester수율 170.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of D-valine benzyl ester free base (12.92 g, 62 mmol) in dry methylene chloride (120 mL) was added 3,4-(methylenedioxy)phenyl methanol (9.45 g, 62 mmol) and sodium triacetoxyborohydride (18.50 g, 86.8 mmol). After 15 h, the reaction mixture was quenched with saturated aqueous sodium bicarbonate (120 mL) and the aqueous layer was separated and extracted with methylene chloride. The combined methylene chloride layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was chromatographed (300 g SiO2, 5% ethyl acetate-hexanes) to afford 2(R)-(3,4-methylenedioxy-benzylamino)-3-methylbutyric acid benzyl ester (18 g) as a colorless oil.

후처리

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate (120 mL)
  2. customthe aqueous layer was separated
  3. extractionextracted with methylene chloride
  4. washThe combined methylene chloride layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed (300 g SiO2, 5% ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-7899147583564fc9b107d96c0c869468
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844366B2

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