Potassium Carbonate → Colestolone

HRID 1199312노트

반응식

HRID 1199312 반응식
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[C:17](=[O:37])[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[C:17](=[O:37])[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 11249146HCID 11249146, 화합물

생성물 1

HCID 10046567Colestolone

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Compound (4) does not show the characteristic streaking of the epoxide (3) by thin layer chromatography, using 10% ethyl acetate/hexane as the solvent system, on silica gel plates, but rather provides a discrete band at an Rf of about 0.1-0.2. The compound treated with a protic acid (preferably 70% perchloric acid) for 2 hours to obtain the precursor (3β,5α)-3-(benzoyloxy)cholest-8(14)en-15-one (6). The precursor (6) is dissolved in a protic solvent, preferably methanol, and treated with potassium carbonate as hereinbefore described to provide the desired product (7). The alternate procedures of Scheme II for the debenzoylation may also be used.

출처 및 근거

ORD 기록
ord-dbac642e3e36401dad3b4d995c8a12db
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04900477

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