Reacción #1772015

Ecuación de reacción

2

Methyl Cyclopentylmandelate

N-methyl-3-pyrrolidinol

EtOAc

EtOH

→

product 4

Rendimiento 72.0%

N-Methyl-3-pyrrolidinyl cyclopentylmandelate

Rendimiento 72.0%

Disolventes

n-heptane

heptane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONhad been distilled
2. 2
   workup.ADDITIONAbout 0.003 g of sodium was added
3. 3
   Temperaturaheated 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
   TemperaturaThe solution was then cooled
7. 7
   Extracciónextracted with 3N HCl
8. 8
   ExtracciónThe acid extract
9. 9
   Extracciónextracted three times with ether
10. 10
    OtroRemoval of the dried ether solution
11. 11
    Otrogave a crude oil

Procedimiento

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.

Fuente