反応 #70376

ord-0b8a3af72edd4232b1ebb05e5f548576

反応方程式

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)-6α-hydroxymethyl-androstane
→
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
収率 96.0%

反応物

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)-6α-hydroxymethyl-androstane

試薬

なし

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

17,17-Bis(ethylendioxy)-6α-(2-hydroxyethyl)androstane was prepared in 96% yield from 3,3:17,17-bis(ethylendioxy)-6α-vinylandrostane by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6α-hydroxymethyl-androstane (Prepn. 14). 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 (1H, t), 3.86-3.70 (8H, m), 3.35 (2H, m), 1.91-0.42 (23H, m), 0.75 (3H, s), 0.74 (3H, s).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08536160B2uspto-grants-2013_09