반응 #1999859

ord-57e43c28166243ca8288574c007a3b19

반응 방정식

C=C[C@H]1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2CC24OCCOC23OCCO4)[C@@]2(C)CCCCC12
17,17-bis(ethylendioxy)-6α-vinylandrostane
C[C@]12CCCCC1[C@H](CO)C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-6β-hydroxymethylandrostane
→
C[C@]12CCCCC1[C@@H](CCO)C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-Bis(ethylendioxy)-6α-(2-hydroxyethyl)androstane
수율 96.0%

반응물

C=C[C@H]1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2CC24OCCOC23OCCO4)[C@@]2(C)CCCCC12
17,17-bis(ethylendioxy)-6α-vinylandrostane
C[C@]12CCCCC1[C@H](CO)C[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-6β-hydroxymethylandrostane

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The crude was purified by flash chromatography (SiO2, n-hexane/acetone 80/20)

실험 절차

17,17-Bis(ethylendioxy)-6α-(2-hydroxyethyl)androstane was prepared in 96% yield from 3,3:17,17-bis(ethylendioxy)-6α-vinylandrostane (Prepn. 11) by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6β-hydroxymethylandrostane (Prepn. 9). The crude was purified by flash chromatography (SiO2, n-hexane/acetone 80/20). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.25 (t, 1H), 3.86-3.70 (m, 8H), 3.35 (m, 2H), 1.91-0.42 (m, 23H), 0.75 (s, 3H), 0.74 (s, 3H).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08609644B2uspto-grants-2013_12