Реакция #1772015

Уравнение реакции

2

Methyl Cyclopentylmandelate

N-methyl-3-pyrrolidinol

EtOAc

EtOH

→

product 4

Выход 72.0%

N-Methyl-3-pyrrolidinyl cyclopentylmandelate

Выход 72.0%

Растворители

n-heptane

heptane

Условия реакции

Обработка

1. 1
   workup.DISTILLATIONhad been distilled
2. 2
   workup.ADDITIONAbout 0.003 g of sodium was added
3. 3
   Температураheated for 2 h as the distillation
4. 4
   workup.ADDITIONMore heptane was added at such a rate as
5. 5
   workup.ADDITIONAdditional sodium was added at the end of an hour
6. 6
   ТемператураThe solution was then cooled
7. 7
   Экстракцияextracted with 3N HCl
8. 8
   ЭкстракцияThe acid extract
9. 9
   Экстракцияextracted three times with ether
10. 10
    ДругоеRemoval of the dried ether solution
11. 11
    Другоеgave a crude oil

Методика

A solution of 2 (2.20 g, 9.4 mmol) and N-methyl-3-pyrrolidinol (3, 1.30 g, 13 mmol) in 40 ml of n-heptane was heated until 20 ml of heptane had been distilled. About 0.003 g of sodium was added, and the solution was stirred and heated for 2 h as the distillation was continued. More heptane was added at such a rate as to keep the reaction volume constant. Additional sodium was added at the end of an hour. The solution was then cooled and extracted with 3N HCl. The acid extract was made alkaline with concentrated NaOH and extracted three times with ether. Removal of the dried ether solution gave a crude oil. Flash chromatography of the crude product on silica gel with 8:1 EtOAc:EtOH gave pure product 4 (2.053 g, 72%). Analysis for C18H25NO3. Calcd: C, 71.26; H, 8.31; N, 4.62. Found: C, 71.55; H, 8.44; N, 4.68. 1H NMR (CDCl3, 500 MHz): 1.27-1.35, 1.40-1.47, 1.54-1.60, 1.75-1.90 [8H, m, (CH2)4], 2.12-2.30, 2.52-2.57, 2.64-2.81 (6H, m CH2NCH2CH2), 2.33, 2.36 (3H, 2s, NCH3), 2.93 [(1H, p, CHC(OH)], 3.83 (1H, bs, OH), 5.23 (1H, m, CO2CH), 7.23-7.36, 7.64-7.67 (5H, m, Ph) ppm.

Источник