Water → HCID 86660496, 화합물

HRID 244251

반응식

HRID 244251 반응식
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH:13]=[CH:12][CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:20].[CH3:21][Mg]Br.O>C1COCC1.C(OCC)(=O)C>[CH3:21][C@@:3]1([OH:20])[CH2:4][CH2:5][C@H:6]2[C@H:7]3[C@H:17]([CH2:18][CH2:19][C@:2]12[CH3:1])[C@:15]1([CH3:16])[CH:10]([CH2:11][CH:12]=[CH:13][CH2:14]1)[CH2:9][CH2:8]3

참가 물질

6

반응물 3

HCID 962WaterHCID 1019285alpha-Androst-2-en-17-oneHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 86660496HCID 86660496, 화합물수율 39%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of compound 2 (300 mg, 1.10 mmol) in anhydrous THF (15 mL) under an atmosphere of argon at 0° C. was added methyl magnesium bromide (1.4 M in THF; 945 μL, 1.32 mmol). The solution was allowed to return to room temperature and was subsequently stirred overnight. The solution was then diluted with ethyl acetate and poured into water. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude compound was purified by high performance flash chromatography (Biotage) using Hexanes/EtOAc (95:5) as eluant to yield compound 27 (123 mg, 39%). 1H NMR (CDCl3) δ: 0.78 (s, 18-CH3), 0.86 (s, 19-CH3), 1.21 (s, 17α-CH3), 0.65-2.05 (residual CH and CH2), 5.59 (m, 2×CH of alkene).

후처리

  1. customto return to room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude compound was purified by high performance flash chromatography (Biotage)

출처 및 근거

ORD 기록
ord-d6f793d5d1f64cca81c7bc349d2c5c27
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653054B2

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