Ethanol → Benzyl [2-(tert-butyldimethylsilyloxy)-4-hydroxy-1,3,3-trimethylbutyl]carbamate

HRID 906976ノート

反応式

HRID 906976 の反応式
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:30])[CH:13]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:14]([CH3:21])([CH3:20])[C:15](OCC)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].C(O)C.[BH4-].[Na+]>C1COCC1.O>[Si:23]([O:22][CH:13]([C:14]([CH3:20])([CH3:21])[CH2:15][OH:16])[CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:30])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

参加物

7

反応物 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 59556980Ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-(tert-butyldimethylsilyloxy)pentanoate

生成物 1

HCID 59273056Benzyl [2-(tert-butyldimethylsilyloxy)-4-hydroxy-1,3,3-trimethylbutyl]carbamate収率 28.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixed solution of ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-(tert-butyldimethylsilyloxy)pentanoate (5.42 g) and calcium chloride (2.06 g) in THF (50 mL)-ethanol (25 mL) was added sodium borohydride (1.56 g) and the mixture was stirred at room temperature for 13 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1) to give the title compound as a colorless solid (yield: 1.38 g, yield: 28%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1)

出典と根拠

ORDレコード
ord-bf17e195bc364db9bea0510bcdfddbd5
出典データセット
uspto-grants-2011_09
特許番号
US08013008B2

反応ノート

読み込み中…