Potassium Carbonate → Colestolone

HRID 1199312ノート

反応式

HRID 1199312 の反応式
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

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 11249146HCID 11249146、化合物

生成物 1

HCID 10046567Colestolone

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-dbac642e3e36401dad3b4d995c8a12db
出典データセット
uspto-grants-1990_02
特許番号
US04900477

反応ノート

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