Reaktion #70395

ord-43683e7f220e466fb71b9ce8bed16c9e

Reaktionsgleichung

C=C1CC2CCCC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC45OCCOC43OCCO5)[C@H]12

17,17-bis(ethylendioxy)-7-methyleneandrostane

C[C@]12CCCCC1C[C@@H](CO)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3

17,17-bis(ethylendioxy)-7α-hydroxymethylandrostane

C[C@]12CCCCC1[C@@H](CO)C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3

17,17-bis(ethylendioxy)-6α-hydroxymethyl-androstane

→

17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane

Ausbeute 70.0%

Edukte

17,17-bis(ethylendioxy)-7-methyleneandrostane

17,17-bis(ethylendioxy)-7α-hydroxymethylandrostane

17,17-bis(ethylendioxy)-6α-hydroxymethyl-androstane

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
SonstigeThe residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40)

Vorschrift

17,17-bis(ethylendioxy)-7α-hydroxymethylandrostane and 3,3:17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane were prepared in 10% and 70% yield, respectively, from 3,3:17,17-bis(ethylendioxy)-7-methyleneandrostane (Prepn. 33, 2.9 g) by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6α-hydroxymethyl-androstane (Prepn. 14). The residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40). 3,3:17,17-bis(ethylendioxy)-7α-hydroxymethylandrostane 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.85-3.75 (8H, m), 3.67 (2H, m), 3.34 (1H, t), 2.00-0.90 (21H, m), 0.87 (3H, s), 0.81 (3H, s) 3,3:17,17-bis(ethylendioxy)-7β-hydroxymethylandrostane 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.90-3.75 (8H, m), 3.58 (2H, m), 3.31 (1H, t), 2.00-1.10 (21H, m), 0.84 (3H, s), 0.81 (3H, s).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536160B2uspto-grants-2013_09