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

HRID 1760801ノート

反応式

HRID 1760801 の反応式
[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

参加物

4

反応物 2

HCID 5049666Sodium triacetoxyborohydrideHCID 7350007Benzyl D-valinate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7899147583564fc9b107d96c0c869468
出典データセット
uspto-grants-2005_01
特許番号
US06844366B2

反応ノート

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