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 1198867

Reaktionsgleichung

Reaktionsgleichung von HRID 1198867
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]

Komponenten

4

Edukt 2

HCID 148012757-(acetyloxy)-alpha-chloro-3a,4,5,6,7,7a-hexahydro-gamma,3a-dimethyl-1H-indene-3-butanoic acid methyl esterHCID 21226445Aluminium lithium hydride2×

Produkt 1

HCID 148012777-(acetyloxy)-beta-chloro-3a,4,5,6,7,7a-hexahydro-delta,3a-dimethyl-1H-indene-3-butanolAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-be3197b084154715bcfb5f8ecb8dd3f3
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04898855

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