Acrivastine → HCID 10360541，化合物

HRID 542502

反应方程式

HRID 542502 反应方程式
[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[N:21]=[C:20](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])[CH:19]=[CH:18][CH:17]=2)\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Ni]>[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[N:21]=[C:20]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:19]=[CH:18][CH:17]=2)\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参与物

3

反应物 1

HCID 5284514Acrivastine

产物 1

HCID 10360541HCID 10360541，化合物

试剂、催化剂与溶剂 1

HCID 935Nickel催化剂

实验过程

A solution of compound 2, vide supra, (3 g) in alcohol (100 mL) containing Raney nickel (1 g) was stirred under hydrogen at room temperature and pressure until the calculated quantity of hydrogen had been absorbed (ca. 45 minutes). The reduced ester was recovered by filtration and evaporation and purified by column chromatography on silica gel using petroleum ether as eluent. Butyllithium (10 mL, 1.64M in hexane) was added under nitrogen to a stirred suspension of triphenyl-2-pyrrolidinoethylphosphonium bromide (7.2 g) in dry toluene (75 mL) to prepare a Wittig reagent. Treatment of this ester with Wittig reagent by the method of Example 1 followed by saponification gave a mixture of two isomeric acids which were separated by fractional crystallization from ethyl acetate/petroleum ether mixtures. The less soluble E isomer, 3-{6-[3-Pyrrolidino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl]-propionic acid (Compound B), melted at 156°-157°.

后处理

  1. custompressure until the calculated quantity of hydrogen had been absorbed (ca. 45 minutes)
  2. filtrationThe reduced ester was recovered by filtration and evaporation
  3. custompurified by column chromatography on silica gel
  4. additionButyllithium (10 mL, 1.64M in hexane) was added under nitrogen to a stirred suspension of triphenyl-2-pyrrolidinoethylphosphonium bromide (7.2 g) in dry toluene (75 mL)
  5. customto prepare a Wittig reagent
  6. customgave
  7. additiona mixture of two isomeric acids which
  8. customwere separated by fractional crystallization from ethyl acetate/petroleum ether

来源与证据

ORD记录
ord-8ce2272845cd4c67afe1d10432f4ba1b
来源数据集
uspto-grants-1987_04
专利号
US04657918

关联笔记

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