Tetrahydrofuran → 21-methylene-20(R)-methylpregn-4-en-3-one

HRID 1107210

反応式

HRID 1107210 の反応式
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2.C(Cl)Cl.[C:24]([O:27]CC)(=[O:26])[CH3:25].[CH2:30]1[CH2:34]O[CH2:32][CH2:31]1>>[CH2:34]=[CH:30][C@@H:31]([CH3:32])[C@@H:3]1[C@:2]2([CH3:1])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C:10](=[CH:11][C:12](=[O:20])[CH2:13][CH2:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1.[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:14]([CH2:13][C:12](=[O:20])[C:11]4[CH:10]=[C:9]([CH2:25][C:24]([O-:27])=[O:26])[CH:8]=[CH:7][C:6]=43)[C@@H:15]1[CH2:17][CH:18]=[CH:19]2

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 92979Androsta-4,16-dien-3-oneHCID 21226138Dichloromethane ethylacetate

生成物 2

HCID 1542966021-methylene-20(R)-methylpregn-4-en-3-one収率 48%HCID 22873077Estra-1,3,5(10),16-tetraen-6-one-3-yl-acetate収率 48%

実験手順

These syntheses are depicted in FIG. 178. Androsta-4,16-dien-3-one (4) was reduced at -55° with 5 lithium tris (1, 2-dimethylpropyl) hydridoborate in THF (c) as described for the preparation of 2 (FIG. 1). Chromatography on silica gel with CH2Cl2 /ethyl acetate 9:1 gave pure axial alcohol 5 (48% yield) and pure equatorial alcohol 6 (48% yield). Analytical samples were further purified by recrystallization (from PE at -30° for 5, from cyclohexane at RT. for 6).

後処理

  1. customas described for the preparation of 2 (FIG. 1)

出典と根拠

ORDレコード
ord-012e58eda95e4b99beabe96aef76749b
出典データセット
uspto-grants-2000_05
特許番号
US06057439

関連ノート

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