تفاعل #70355

ord-44a31d2c1cb54fe18b641b7ac37397c9

معادلة التفاعل

C[C@]12CCC(=O)C=C1/C(=N/O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6-(E)-hydroxyiminoandrost-4-ene-3,17-dione
Cl.Cl.NO[C@H]1CCNC1
3-(S)-pyrrolidinyloxyamine dihydrochloride
→
C[C@]12CCC(=NO[C@H]3CCNC3)C=C1/C(=N/O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
title compound
المردود 65.0%
C[C@]12CCC(=NO[C@H]3CCNC3)C=C1/C(=N/O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3-[3-(S)-Pyrrolidinyl]oxyimino-6-(E)-hydroxyiminoandrost-4-ene-17-one
المردود 65.0%

المتفاعلات

C[C@]12CCC(=O)C=C1/C(=N/O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6-(E)-hydroxyiminoandrost-4-ene-3,17-dione
Cl.Cl.NO[C@H]1CCNC1
3-(S)-pyrrolidinyloxyamine dihydrochloride

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe crude product (1/1 ratio of the E/Z isomers) was purified by flash chromatography (SiO2, CH2Cl2/MeOH/26% NH4OH 90/10/1)
  2. 2
    أخرىThe less polar fractions were evaporated to dryness

الإجراء التجريبي

The title compound I-dw was obtained following the procedure described in Example 100 and starting from 6-(E)-hydroxyiminoandrost-4-ene-3,17-dione (II-bw, Prepn. 63, 200 mg) and 3-(S)-pyrrolidinyloxyamine dihydrochloride (III-d, Prepn. 4) (110 mg). The crude product (1/1 ratio of the E/Z isomers) was purified by flash chromatography (SiO2, CH2Cl2/MeOH/26% NH4OH 90/10/1). The less polar fractions were evaporated to dryness to give the title compound I-dw in 65% yield. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.72 (1H, bs), 6.16 (1H, bs), 4.69 (1H, m), 3.36-3.10 (7H, m), 2.60-1.10 (16H, m), 0.96 (3H, s), 0.83 (3H, s).

المصدر

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