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

HRID 388753

반응식

HRID 388753 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21877217Toluene methylene chloride용매

반응 조건

온도
-78 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-97a066058c514960a49340a7efea8c0d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377913B2

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