Formic Acid → 5beta-Pregn-3-en-20-one

HRID 867085

反応式

HRID 867085 の反応式
[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:23])[CH2:9][CH2:10][C@@H:11]3[C@:21]4([CH3:22])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=O)[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].C(O)=O.CCCCC>C(Cl)Cl.[Zn]>[CH3:1][C:2](=[O:3])[C@@H:4]1[C@:8]2([CH3:23])[C@H:7]([C@H:12]3[C@H:11]([CH2:10][CH2:9]2)[C@:21]2([CH3:22])[C@@H:15]([CH:16]=[CH:17][CH2:19][CH2:20]2)[CH2:14][CH2:13]3)[CH2:6][CH2:5]1

参加物

6

反応物 3

HCID 284Formic AcidHCID 5994ProgesteroneHCID 8003Pentane

生成物 1

HCID 706184365beta-Pregn-3-en-20-one収率 41.5%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 250 mg of progesterone, 7.5 g of zinc dust, 18.75 ml of methylene chloride and 6.25 ml of 90% formic acid was shaken at room temperature for 18 hours, whereupon it was worked up by the procedure described in Example 36. Concentration of a solution of the crude product in methylene chloride with intermittent addition of pentane gave 99.18 mg of 5β-pregn-3-en-20-one, mp 135°-136.5°, 139.5° C., nmr (CDCl3,δ) 5.5 (2, broadened dd; 3--H, 3--H, 4--H), 2.12 (3, S; 21--H) 0.96 (3, S; 19--H), 0.77 (trace, S; 19--H of 5α-isomer?) and 0.61 (3, S; 18--H) ppm.

出典と根拠

ORDレコード
ord-26112cbdbd5141e8a5f763b0f39980dc
出典データセット
uspto-grants-1978_07
特許番号
US04102884

関連ノート

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