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 6282Notes

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-3b52f1fff38f4058ba6f446cfd607f7d
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05247123

Reaction notes

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