Ammonia → Oxendolone

HRID 1154783

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HRID 1154783 반응식
[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]

참가 물질

6

반응물 4

HCID 222Ammonia2회HCID 8028TetrahydrofuranHCID 3028194LithiumHCID 12831647HCID 12831647, 화합물

생성물 1

HCID 443947Oxendolone

시약·촉매·용매 1

HCID 6386tert-Butanol용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a7e1eac35c894d3aabd07696fa222da2
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04298538

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