加巴喷丁 → Prop-2-enyl 2-[1-(aminomethyl)cyclohexyl]acetate;hydrochloride

HRID 30515

反应方程式

HRID 30515 反应方程式
[CH2:1]1[CH2:6][CH2:5][C:4]([CH2:11][NH2:12])([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.[CH2:13](O)[CH:14]=[CH2:15].S(Cl)([Cl:19])=O>C(OCC)C>[ClH:19].[NH2:12][CH2:11][C:4]1([CH2:7][C:8]([O:10][CH2:15][CH:14]=[CH2:13])=[O:9])[CH2:3][CH2:2][CH2:1][CH2:6][CH2:5]1

参与物

5

反应物 3

HCID 3446加巴喷丁HCID 7858丙烯醇HCID 24386氯化亚砜

产物 1

HCID 66743418Prop-2-enyl 2-[1-(aminomethyl)cyclohexyl]acetate;hydrochloride收率 88.8%

试剂、催化剂与溶剂 1

HCID 3283乙醚溶剂

反应条件

温度
0 °C

实验过程

A dry 500 mL, three-neck, round-bottomed flask was fitted with a magnetic stirring bar and a 100 mL pressure-equalizing addition funnel and flushed with nitrogen gas. The flask was charged with gabapentin (17.1 g, 0.1 mol) and allyl alcohol (100 mL, 1.46 mol) and the entire mixture was cooled to 0° C. in an ice-water bath. Thionyl chloride (22.5 mL, 36 g, 0.3 mol) was added drop-wise over a period of 30 min to the stirred solution, and the reaction mixture allowed to stir for 16 h at room temperature. The mixture was then diluted with diethyl ether (200 mL) and cooled to 0° C. while stirring. After several minutes white crystals formed, and were collected by filtration. The crude compound was recrystallized from a mixture of ethanol and diethyl ether (50 mL: 150 mL) to give the product (13) as a white solid (22 g, 88% yield), m.p: 138-142° C. 1H NMR (CD3OD, 400 MHz): δ 1.36-1.54 (m, 10H), 2.57 (s, 2H), 3.05 (s, 2H), 4.61 (d, 2H), 5.22 (dd, 1H), 5.33 (dd, 1H), 5.90-6.00 (m, 1H). MS (ESI) m/z 212.0 (M+H+).

后处理

  1. customA dry 500 mL, three-neck, round-bottomed flask was fitted with a magnetic stirring bar and a 100 mL pressure-equalizing addition funnel
  2. customflushed with nitrogen gas
  3. temperaturecooled to 0° C.
  4. stirringwhile stirring
  5. customAfter several minutes white crystals formed
  6. filtrationwere collected by filtration
  7. customThe crude compound was recrystallized from a mixture of ethanol and diethyl ether (50 mL: 150 mL)

来源与证据

ORD记录
ord-82e707b05926446ba4ee960a9601be13
来源数据集
uspto-grants-2008_09
专利号
US07423169B2

关联笔记

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