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

HRID 388753

Reaction equation

[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

Participants

Conditions

Temperature: -78 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-97a066058c514960a49340a7efea8c0d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377913B2

Linked notes

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