Ammonia → Oxendolone

HRID 1154783

反応式

HRID 1154783 の反応式
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[OH:23])[C:17]1[CH:16]=[CH:15][C:14]([O:21]C)=[CH:13][C:12]=1[CH2:11][CH2:10]3)[CH3:2].O1CCCC1.N.[Li]>C(O)(C)(C)C>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[OH:23])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

参加物

6

反応物 4

HCID 222Ammonia2 回HCID 8028TetrahydrofuranHCID 3028194LithiumHCID 12831647HCID 12831647、化合物

生成物 1

HCID 443947Oxendolone

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
50 °C

実験手順

A solution of 2.0 g. of 16β-ethyl-3-methoxy-1,3,5(10)-estratrien-17β-ol in 40 ml. of tetrahydrofuran and 4 ml. of tert.-butanol is added dropwise at -40° C. to 80 ml. of ammonia. After the incremental introduction of 1.2 g. of lithium, the mixture is stirred for 2 hours at -40° C.; then the ammonia is allowed to evaporate, the residue is poured into about 200 ml. of water, and the mixture is extracted with ethyl acetate. The crude product is taken up in 40 ml. of methanol and 4 ml. of 4 N hydrochloric acid and agitated for 15 minutes at 50° C. Thereafter, the mixture is poured into water and extracted with methylene chloride. After recrystallizing the crude product from ethyl acetate/ether, 1.7 g. of 16β-ethyl-17β-hydroxy-4-estren-3-one is produced, m.p. 150°-152° C.

後処理

  1. customto evaporate
  2. additionthe residue is poured into about 200 ml
  3. extractionof water, and the mixture is extracted with ethyl acetate
  4. additionThereafter, the mixture is poured into water
  5. extractionextracted with methylene chloride
  6. customAfter recrystallizing the crude product from ethyl acetate/ether, 1.7 g

出典と根拠

ORDレコード
ord-a7e1eac35c894d3aabd07696fa222da2
出典データセット
uspto-grants-1981_11
特許番号
US04298538

関連ノート

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