Water → (2beta,3alpha)-3-Hydroxy-2-(piperazin-1-yl)androstan-17-one

HRID 244249노트

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HRID 244249 반응식
[O:1]1[C@H:3]2[CH2:4][CH:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C:12](=[O:21])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.O.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>ClCCl>[OH:1][C@@H:3]1[C@@H:2]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:19][C@@:18]2([CH3:20])[CH:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:21])[CH2:4]1

참가 물질

5

반응물 3

HCID 962WaterHCID 4837PiperazineHCID 86660494(2alpha,3alpha)-2,3-Epoxyandrostan-17-one

생성물 1

HCID 86660495(2beta,3alpha)-3-Hydroxy-2-(piperazin-1-yl)androstan-17-one수율 65%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
150 °C

실험 절차

To compound 22 (202 mg, 0.70 mmol) was added water (1 mL) and piperazine (3.5 g, 41 mmol). The solution was subsequently heated at 150° C. over a period of 24 h. The resulting mixture was diluted with dichloromethane (50 mL) and washed with water, dried with Na2SO4, filtered and evaporated under reduced pressure. The crude compound was purified by flash chromatography (DCM/MeOH: 9:1 containing 0.5% of TEA) to yield compound 23 (169 mg, 65%). 1H NMR (CDCl3) δ: 0.87 (s, 18-CH3 and 19-CH3), 0.73-2.17 (residual CH and CH2), 2.45, 2.64 and 2.91 (3m, 4×CH2N and 2α-CH), 3.85 (m, 3β-CH).

후처리

  1. washwashed with water
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude compound was purified by flash chromatography (DCM/MeOH: 9:1 containing 0.5% of TEA)

출처 및 근거

ORD 기록
ord-9c870cd54c6c47a58d6513727bb6eaac
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653054B2

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