(Dimethyl sulfide)trihydroboron → [2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol

HRID 916068ノート

反応式

HRID 916068 の反応式
CSC.B.C[O:6][C:7](=O)[C:8]1[CH:13]=[C:12]([C@@H:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:15][Br:16])[CH:11]=[CH:10][C:9]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[CH2:26]([O:25][C:9]1[CH:10]=[CH:11][C:12]([C@@H:14]([O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20])[CH2:15][Br:16])=[CH:13][C:8]=1[CH2:7][OH:6])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

4

反応物 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 57438683Methyl 2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy]ethyl)benzoate

生成物 1

HCID 12988834[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol収率 80.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Borane dimethylsulfide complex (42.4 ml of 10M solution in tetrahydrofuran, 424 mmol) was added dropwise to a solution methyl-2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)benzoate (Preparation 40) (91.0 g, 189 mmol) in tetrahydrofuran (1600 ml). The resulting mixture was then heated to reflux for 2 hours and then cooled to 0° C. before quenching with methanol (270 ml). The mixture was left to stir at room temperature for 16 hours and then the solvent removed in vacuo. The residue was partitioned between dichloromethane (500 ml) and water (500 ml). The aqueous phase was separated and extracted with dichloromethane (500 ml) and the combined organic extracts washed with brine (500 ml), dried (magnesium sulfate) and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica gel eluting with cyclohexane:ethyl acetate (100:0 changing to 80:20, by volume) to give the title compound (68.7 g) as a colourless oil.

後処理

  1. temperatureThe resulting mixture was then heated
  2. temperatureto reflux for 2 hours
  3. custombefore quenching with methanol (270 ml)
  4. waitThe mixture was left
  5. customthe solvent removed in vacuo
  6. customThe residue was partitioned between dichloromethane (500 ml) and water (500 ml)
  7. customThe aqueous phase was separated
  8. extractionextracted with dichloromethane (500 ml)
  9. washthe combined organic extracts washed with brine (500 ml)
  10. dry with materialdried (magnesium sulfate)
  11. customthe solvent removed in vacuo
  12. customThe residue was purified by flash column chromatography on silica gel eluting with cyclohexane:ethyl acetate (100:0 changing to 80:20, by volume)

出典と根拠

ORDレコード
ord-84aadd6ca3fa453b8ce9b174a59bf4fa
出典データセット
uspto-grants-2007_09
特許番号
US07268147B2

反応ノート

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