Water → (2beta,3alpha,17beta)-17-Methoxv-2-(piperazin-1-yl)androstan-3-ol

HRID 244255노트

반응식

HRID 244255 반응식
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[CH:12]([CH2:13][C@@H:14]2[O:22][C@@H:15]2[CH2:16]1)[CH2:11][CH2:10]3.O.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>ClCCl>[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[CH:12]([CH2:13][C@H:14]([OH:22])[C@@H:15]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:16]1)[CH2:11][CH2:10]3

참가 물질

5

반응물 3

HCID 962WaterHCID 4837PiperazineHCID 86660499(2alpha,3alpha,17beta)-17-Methoxy-2,3-epoxyandrostane

생성물 1

HCID 86660501(2beta,3alpha,17beta)-17-Methoxv-2-(piperazin-1-yl)androstan-3-ol수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
150 °C

실험 절차

To compound 35 (100 mg, 0.33 mmol) was added water (1 mL) and piperazine (3.5g, 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 36 (90 mg, 70%). 1H NMR (CDCl3) δ: 0.72 (s, 18-CH3), 0.82 (s, 19-CH3), 0.65-2.05 (residual CH and CH2), 2.38, 2.60 and 2.86 (3m, 4×CH2N and 2α-CH), 3.18 (t, J=8.2 Hz, 17α-CH), 3.31 (s, OCH3), 3.82 (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-c2526a81e14946bf9f0ee570062773cf
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653054B2

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