Water → (2beta,3alpha,17beta)-17-Methyl-2-(piperazin-1-yl)androstane-3,17-diol

HRID 244253노트

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HRID 244253 반응식
[CH3:1][C@@:2]1([OH:22])[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[CH:11]([CH2:12][C@@H:13]2[O:21][C@@H:14]2[CH2:15]1)[CH2:10][CH2:9]3.O.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>ClCCl>[CH3:1][C@@:2]1([OH:22])[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[CH:11]([CH2:12][C@H:13]([OH:21])[C@@H:14]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:15]1)[CH2:10][CH2:9]3

참가 물질

5

반응물 3

HCID 962WaterHCID 4837PiperazineHCID 86660497(2alpha,3alpha,17beta)-17-Methyl-2,3-epoxyandrostan-17-ol

생성물 1

HCID 86660498(2beta,3alpha,17beta)-17-Methyl-2-(piperazin-1-yl)androstane-3,17-diol수율 60.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
150 °C

실험 절차

To compound 28 (103 mg, 0.34 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 1.0% of TEA) to yield compound 29 (80 mg, 60%). 1H NMR (CDCl3) δ: 0.85 and 0.86 (2s, 18-CH3 and 19-CH3), 1.20 (s, 17α-CH3) 0.65-1.90 (residual CH and CH2), 2.50-3.30 (broad m, 2×CH2N, 2×CH2NH 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 1.0% of TEA)

출처 및 근거

ORD 기록
ord-3d841c0f51244ed48a86249e5fc30fa7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653054B2

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