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 1003177노트

반응식

HRID 1003177 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 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of estrone (11, 2.70 g, 10 mmol) in DMF (40 mL) were added potassium carbonate (2.76 g, 20 mmol) and benzyl bromide (1.8 mL, 15 mmol) at room temperature. The reaction mixture was stirred for 26 h, then quenched with H2O, and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was washed with Et2O to afford 2.91 g of 40 (81% yield) mp: 126-127° C.

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 (Na2SO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. washThe residue was washed with Et2O

출처 및 근거

ORD 기록
ord-4df41eff0894482a8c483aad11a6afcd
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046186

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