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

HRID 244253ノート

反応式

HRID 244253 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3d841c0f51244ed48a86249e5fc30fa7
出典データセット
uspto-grants-2014_02
特許番号
US08653054B2

反応ノート

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