7-(acetyloxy)-alpha-chloro-3a,4,5,6,7,7a-hexahydro-gamma,3a-dimethyl-1H-indene-3-butanoic acid methyl ester → 7-(acetyloxy)-beta-chloro-3a,4,5,6,7,7a-hexahydro-delta,3a-dimethyl-1H-indene-3-butanol

HRID 1198867Notes

Reaction equation

C[O:2][C:3](=O)[CH:4]([Cl:22])[CH2:5][CH:6]([CH3:21])[C:7]1[C:15]2([CH3:16])[CH:10]([CH:11]([O:17][C:18](=[O:20])[CH3:19])[CH2:12][CH2:13][CH2:14]2)[CH2:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:18]([O:17][CH:11]1[CH:10]2[C:15]([CH3:16])([C:7]([CH:6]([CH3:21])[CH2:5][CH:4]([Cl:22])[CH2:3][OH:2])=[CH:8][CH2:9]2)[CH2:14][CH2:13][CH2:12]1)(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.01 g (2.95 mmol) of [3aS-[3(αS*,γR*),3aα,7β,7aβ]-7-(acetyloxy)-α-chloro-3a,4,5,6,7,7a-hexahydro-γ,3a-dimethyl-1H-indene-3-butanoic acid methyl ester in 25 mL of anhydrous tetrahydrofuran was cooled at 0° C. and treated under argon with 1.47 mL (1.47 mmol) of a 1M solution of lithium aluminum hydride in tetrahydrofuran. After stirring for 2 hours at 0° C., additional 0.20 mL of lithium aluminum hydride solution was added and the reaction allowed to proceed for 1 additional hour. It was then quenched by careful addition of 8 mL of a 2N aqueous Rochelle salt solution, then 0.5 mL of 2N hydrochloric acid. After dilution with water, it was extracted with ethyl acetate. The combined extracts were washed with 2N aqueous Rochelle salt solution, then brine, dried and evaporated to dryness to give 0.90 g (93% yield) of the title compound as a colorless, thick oil: [α]23D-30.1° (c 0.6, EtOH); 1H NMR (200 MHz, CDCl3) δ0.93 (s, 3H), 1.07 (d, J=7.2 Hz, 3H), 2.04 (s, 3H), 2.52 (br m, 1H), 3.73 (m, 2H), 4.00 (m, 1H), 4.97 (td, J=12.0, 4.4 Hz, 1H), 5.27 (br s, 1H) ppm.

Workup

customIt was then quenched by careful addition of 8 mL of a 2N aqueous Rochelle salt solution
extractionAfter dilution with water, it was extracted with ethyl acetate
washThe combined extracts were washed with 2N aqueous Rochelle salt solution
dry with materialbrine, dried
customevaporated to dryness

Sources & evidence

ORD record: ord-be3197b084154715bcfb5f8ecb8dd3f3
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04898855

Reaction notes

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