3,4-dihydro-2H-pyran → 3beta-(2-Tetrahydropyranoxy)androst-5-ene-7,17-dione

HRID 551839

반응식

HRID 551839 반응식
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[C:12]([CH:14]=[C:15]3[CH2:20][C@@H:19]([OH:21])[CH2:18][CH2:17][C@:16]3([CH3:22])[C@H:5]1[CH2:4][CH2:3]2)=[O:13].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:40]1[CH:45]=[CH:44][CH2:43][CH2:42][CH2:41]1>>[O:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH:41]1[O:21][C@H:19]1[CH2:18][CH2:17][C@@:16]2([CH3:22])[C:15](=[CH:14][C:12](=[O:13])[C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:20]1

참가 물질

4

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 1933137-Keto-dehydroepiandrosteroneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

생성물 1

HCID 697363133beta-(2-Tetrahydropyranoxy)androst-5-ene-7,17-dione

실험 절차

3β-hydroxyandrost-5-ene-7,17-dione (2) (0.5 g, 1.65 mmol) was placed in a dried, argon-flushed flask where it was dissolved in dry dichloromethane (20.0 mL). Pyridinium toluene-p-sulfonate (0.043 g. 0.17 mmol) was added followed by 3,4-dihydro-2H-pyran (0.23 mL, 2.5 mmol) and the solution was stirred at room temperature, under an atmosphere of argon, for 2-3 h. The reaction was quenched by adding water and the product was extracted thrice with ether (3×20 mL). The combined ether extracts were washed with dilute acetic acid, water and bicarbonate solution and dried (MgSO4). Solvent was removed and the crude product was purified using chromatography on silica gel (ethyl acetate-hexane, 15:85, v/v). The compound first eluted was identified as androsta-3,5-diene-7,17-dione (0.150 g), m.p. 167-8° C.

후처리

  1. customflushed flask where it
  2. dissolutionwas dissolved in dry dichloromethane (20.0 mL)
  3. customThe reaction was quenched
  4. additionby adding water
  5. extractionthe product was extracted thrice with ether (3×20 mL)
  6. washThe combined ether extracts were washed with dilute acetic acid, water and bicarbonate solution
  7. dry with materialdried (MgSO4)
  8. customSolvent was removed
  9. customthe crude product was purified
  10. washThe compound first eluted

출처 및 근거

ORD 기록
ord-963224c3229448e38d54c7f58113781d
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947846B2

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