Nandrolone → (+)-Estr-4-ene-3,17-dione

HRID 352310

반응식

HRID 352310 반응식
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@H:20]([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3>C(O)(=O)C>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:12][CH2:13][C:14]4[C@@H:20]3[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=4)[C@@H:7]1[CH2:8][CH2:9][C:10]2=[O:11]

참가 물질

3

반응물 1

HCID 9904Nandrolone

생성물 1

HCID 92834(+)-Estr-4-ene-3,17-dione수율 95%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

To a solution of 19-nortestosterone 52 (26.85 g, 97.85 mmol) in acetic acid (200 mL) was added a CrO3 (7.4 g, 74 mmol) in acetic acid (150 mL) and stirred for 1 h at room temperature. The reaction mixture was concentrated under reduced pressure to half of its initial volume, poured into 1 M hydrochloric acid (500 mL) and extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3, dried over anhydrous MgSO4, filtered, and then concentrated to afford dione 53 as a white solid (25.3 g, 95%): 1H NMR (300 MHz, CDCl3) δ0.94 (s, 3, CH3), 5.85 (s, 1).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure to half of its initial volume
  2. additionpoured into 1 M hydrochloric acid (500 mL)
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with saturated aqueous NaHCO3
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-933ea3556e2945b7973335b3825152d2
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747018B2

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