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

HRID 551839

反応式

HRID 551839 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-963224c3229448e38d54c7f58113781d
出典データセット
uspto-grants-2011_05
特許番号
US07947846B2

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