Hydrochloric Acid → 5alpha-Pregn-2-en-20-one

HRID 2253807

반응식

HRID 2253807 반응식
C1(C)C=CC(S(O[C@@H:11]2[CH2:30][CH2:29][C@@:28]3([CH3:31])[C@@H:13]([CH2:14][CH2:15][C@@H:16]4[C@@H:27]3[CH2:26][CH2:25][C@@:24]3([CH3:32])[C@H:17]4[CH2:18][CH2:19][C@@H:20]3[C:21](=[O:23])[CH3:22])[CH2:12]2)(=O)=O)=CC=1.Cl>N1C(C)=CC(C)=CC=1C>[CH3:22][C:21](=[O:23])[C@@H:20]1[C@:24]2([CH3:32])[C@H:17]([C@H:16]3[C@H:27]([CH2:26][CH2:25]2)[C@:28]2([CH3:31])[C@H:13]([CH2:12][CH:11]=[CH:30][CH2:29]2)[CH2:14][CH2:15]3)[CH2:18][CH2:19]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 538852373alpha-Toluene-p-sulphonyloxy-5alpha-pregnan-20-one

생성물 1

HCID 2468835alpha-Pregn-2-en-20-one수율 97%

시약·촉매·용매 1

HCID 79532,4,6-Trimethylpyridine용매

실험 절차

The crude product 3α-toluene-p-sulphonyloxy-5α-pregnan-20-one in 30 mL of collidine was refluxed for 1.0 h. The solution was allowed to cool and then poured into cold dilute hydrochloric acid (200 mL) and extracted three times with CH2Cl2 (100 mL portions). The combined organic phase was dried over magnesium sulfate and concentrated. Flash chromatography on a silica gel bed (100 g) and elution with hexane/ethyl acetate (80:20) gave 4.65 g (97% yield for the two steps) of 5α-pregn-2-ene-20-one.

후처리

  1. temperatureto cool
  2. extractionextracted three times with CH2Cl2 (100 mL portions)
  3. dry with materialThe combined organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. washFlash chromatography on a silica gel bed (100 g) and elution with hexane/ethyl acetate (80:20)

출처 및 근거

ORD 기록
ord-650dd25937974c86b884e9a3f00bd814
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05232917

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