盐酸 → (+/-)-1-Propionylamino-4-hydroxymethyl-2-cyclopentene

HRID 1069796笔记

反应方程式

HRID 1069796 反应方程式
[C:1]([N:5]1[C:10](=[O:11])[CH:9]2[CH2:12][CH:6]1[CH:7]=[CH:8]2)(=[O:4])[CH2:2][CH3:3].CC(O)CC.[BH4-].[Na+].Cl>O>[C:1]([NH:5][CH:6]1[CH2:12][CH:9]([CH2:10][OH:11])[CH:8]=[CH:7]1)(=[O:4])[CH2:2][CH3:3]

参与物

6

反应物 4

HCID 313盐酸HCID 6568仲丁醇HCID 4311764硼氢化钠HCID 22673281(+/-)-2-Propionyl-2-azabicyclo[2.2.1]hept-5-en-3-one

产物 1

HCID 22673282(+/-)-1-Propionylamino-4-hydroxymethyl-2-cyclopentene收率 65.3%

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次

反应条件

温度
10 °C

实验过程

16.6 g of (±)-2-propionyl-2-azabicyclo[2.2.1]-hept-5-en-3-one were dissolved in water (140 ml) and 2-butanol (66 ml) under nitrogen and cooled to −5° C. 3 g of sodium borohydride were added in portions over the course of 2 h. The mixture was stirred at 10° C. for 2.5 h and then adjusted to pH 2.2 with a mixture of conc. hydrochloric acid and water (1/1). The solution was evaporated to 40 g and adjusted to pH 6.2 with 2N NaOH. The mixture was extracted with 5×50 ml of dichloromethane. The combined organic phases were completely evaporated, and the residue was recrystallized in toluene (150 ml). 11.1 g of title compound were obtained. The yield was 65%.

后处理

  1. customThe solution was evaporated to 40 g
  2. extractionThe mixture was extracted with 5×50 ml of dichloromethane
  3. customThe combined organic phases were completely evaporated
  4. customthe residue was recrystallized in toluene (150 ml)

来源与证据

ORD记录
ord-59e26be1319c44019ed19b3a6e7e72f2
来源数据集
uspto-grants-2001_06
专利号
US06252112B1

反应笔记

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