تفاعل #70383

ord-c70e028c83024678a5ac724e041eeac4

معادلة التفاعل

$C[C@]12CC[C@H]3[C@@H](C/C(=N\O)[C@@]4(O)CCCC[C@]34C)[C@@H]1CC13OCCOC12OCCO3$

17,17-bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyiminoandrostane

C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12

6-methyleneandrostane-3,17-dione

→

$C[C@]12CC[C@H]3[C@@H](C/C(=N\O)[C@@]4(O)CC(=O)CC[C@]34C)[C@@H]1CCC2=O$

title compound

المردود 80.0%

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5α-Hydroxy-6-(E)-hydroxyiminoandrostane-3,17-dione

المردود 80.0%

المتفاعلات

$C[C@]12CC[C@H]3[C@@H](C/C(=N\O)[C@@]4(O)CCCC[C@]34C)[C@@H]1CC13OCCOC12OCCO3$

17,17-bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyiminoandrostane

6-methyleneandrostane-3,17-dione

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية

See reaction.notes.procedure_details.

المعالجة

1
غسيلThe combined organic extracts were washed with H2O
2
تجفيفdried over Na2SO4
3
أخرىevaporated to dryness
4
أخرىThe residue was purified by flash chromatography (SiO2, n-hexane/acetone/CH2Cl2 60/20/20)

الإجراء التجريبي

The title compound II-aq was prepared in 80% yield from 3,3:17,17-bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyiminoandrostane by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (I-ac, Prepn. 13). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone/CH2Cl2 60/20/20). 1H-NMR (300 MHz, acetone-d6, ppm from TMS: δ 10.72 (1H, s), 5.35 (1H, s), 3.12 (1H, dd), 2.85-1.09 (18H, m), 0.94 (3H, s), 0.78 (3H, s).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08536160B2uspto-grants-2013_09