Estrone → (8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

HRID 1243298노트

반응식

HRID 1243298 반응식
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[CH2:27]([O:20][C:9]1[CH:8]=[CH:7][C:6]2[C@@H:5]3[C@H:14]([C@H:15]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 3

HCID 5870EstroneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

생성물 1

HCID 11132151(8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of oestrone (3.35 g, 12.39 mmol) in DMF (50 ml) were added potassium carbonate (3.45 g, 25 mmol) and benzyl bromide (2.25 ml, 18.75 mmol) at room temperature under an atmosphere of nitrogen. The reaction mixture was stirred for 24 h, then quenched with H2O, and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (MgSO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was triturated with Et2O, filtered and evaporated to afford 3.48 g (78% yield) of 3-benzyloxyestra-1,3,5(10)-trien-17-one BLE99049 as a white solid.

후처리

  1. customquenched with H2O
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. customThe residue was triturated with Et2O
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-25df7e296b534f039be29a4db2696a85
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119081B2

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