Diisobutylaluminumhydride → (2e)-2-((3r,5s)-3-{[Tert-butyl(diphenyl)silyl]oxy}-5-fluoro-4-methylenecyclohexylidene)ethanol

HRID 388753ノート

反応式

HRID 388753 の反応式
[Si:1]([O:18][C@H:19]1[C:24](=[CH2:25])[C@@H:23]([F:26])[CH2:22]/[C:21](=[CH:27]/[C:28](OC)=[O:29])/[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl.C1(C)C=CC=CC=1>[Si:1]([O:18][C@H:19]1[C:24](=[CH2:25])[C@@H:23]([F:26])[CH2:22]/[C:21](=[CH:27]/[CH2:28][OH:29])/[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 131730231methyl (2E)-((3R,5S)-3-{[tert-butyl(diphenyl)silyl]oxy}-5-fluoro-4-methylenecyclohexylidene)acetate

生成物 1

HCID 68940324(2e)-2-((3r,5s)-3-{[Tert-butyl(diphenyl)silyl]oxy}-5-fluoro-4-methylenecyclohexylidene)ethanol収率 95%

試薬・触媒・溶媒 1

HCID 21877217Toluene methylene chloride溶媒

反応条件

温度
-78 °C

実験手順

The compound of Example 18B (130 mg, 0.3 mmol) was dissolved in 1 mL of 1:1 dichloromethane/toluene and cooled to −78° C. Diisobutylaluminum hydride (1 M in hexanes, 0.7 mL, 2.5 equivalents) was added, and the mixture was stirred for 30 minutes. Reaction was quenched by the addition of methanol, followed by saturated aqueous NH4Cl; the mixture was warmed to ambient temperature and extracted with ethyl acetate. The organics were washed with brine and dried over Na2SO4. The solvents were removed in vacuo; the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with 15% ethyl acetate in hexanes, to give the titled compound (111 mg, 95%).

後処理

  1. customReaction
  2. customwas quenched by the addition of methanol
  3. temperaturethe mixture was warmed to ambient temperature
  4. extractionextracted with ethyl acetate
  5. washThe organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvents were removed in vacuo
  8. customthe residue was purified by chromatography on an Analogix Intelliflash 280™
  9. washeluting with 15% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-97a066058c514960a49340a7efea8c0d
出典データセット
uspto-grants-2013_02
特許番号
US08377913B2

反応ノート

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