苄氧基胺盐酸盐 → HCID 178419047，化合物

HRID 9331笔记

反应方程式

HRID 9331 反应方程式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6](SC)[C:5]12[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[CH2:19]([O:26][N:27]=[C:6]1[C:5]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[NH:7]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参与物

4

反应物 2

HCID 102312苄氧基胺盐酸盐HCID 219862665'-Bromo-2'-(methylthio)spiro[cyclohexane-1,3'-[3H]indole]

产物 1

HCID 178419047HCID 178419047，化合物

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

反应条件

温度
45 °C

实验过程

5′-Bromo-2′-(methylthio)spiro[cyclohexane-1,3′-[3H]indole] (9.0 g, 28.98 mmol) and O-benzylhydroxylamine hydrochloride (13.8 g, 86.9 mmol) were combined in methanol (150 mL) and heated to 45° C. for 6 hours. Methanol was evaporated in vacuo. Ethyl acetate was added to the residue and this mixture was washed with ammonium chloride solution. Ethyl acetate was dried over magnesium sulfate, ethyl acetate collected evaporated in vacuo and the residue was flash chromatographed on alumina 90 (9:1 Hexane/EtOAc) to the desired product (6.5 g, 60%). 1H NMR (DMSO-d6, 300 MHz) δ 1.38–1.70 (m, 8H), 1.92–2.06 (m, 2H), 5.06 (s, 2H), 6.71 (d, 1H, J=8.26 Hz), 7.22–7.43 (m, 7H), 9.62 (s, 1H).

后处理

  1. customMethanol was evaporated in vacuo
  2. additionEthyl acetate was added to the residue
  3. washthis mixture was washed with ammonium chloride solution
  4. dry with materialEthyl acetate was dried over magnesium sulfate, ethyl acetate
  5. customcollected
  6. customevaporated in vacuo
  7. customchromatographed on alumina 90 (9:1 Hexane/EtOAc) to the desired product (6.5 g, 60%)

来源与证据

ORD记录
ord-2a5db7c4f64e47bcb8b812a4d9f7db0b
来源数据集
uspto-grants-2006_08
专利号
US07091234B2

反应笔记

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