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 6282

Reaktionsgleichung

Reaktionsgleichung von HRID 6282
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-3b52f1fff38f4058ba6f446cfd607f7d
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05247123

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