تفاعل #1772015

معادلة التفاعل

2

Methyl Cyclopentylmandelate

N-methyl-3-pyrrolidinol

EtOAc

EtOH

→

product 4

المردود 72.0%

N-Methyl-3-pyrrolidinyl cyclopentylmandelate

المردود 72.0%

المذيبات

n-heptane

heptane

ظروف التفاعل

المعالجة

1. 1
   workup.DISTILLATIONhad been distilled
2. 2
   workup.ADDITIONAbout 0.003 g of sodium was added
3. 3
   درجة الحرارةheated 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
   درجة الحرارةThe solution was then cooled
7. 7
   استخلاصextracted with 3N HCl
8. 8
   استخلاصThe acid extract
9. 9
   استخلاصextracted three times with ether
10. 10
    أخرىRemoval of the dried ether solution
11. 11
    أخرىgave a crude oil

الإجراء التجريبي

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.

المصدر