Réaction #1772015

Équation de réaction

2

Methyl Cyclopentylmandelate

N-methyl-3-pyrrolidinol

EtOAc

EtOH

→

product 4

Rendement 72.0%

N-Methyl-3-pyrrolidinyl cyclopentylmandelate

Rendement 72.0%

Solvants

n-heptane

heptane

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONhad been distilled
2. 2
   workup.ADDITIONAbout 0.003 g of sodium was added
3. 3
   Températureheated 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
   TempératureThe solution was then cooled
7. 7
   Extractionextracted with 3N HCl
8. 8
   ExtractionThe acid extract
9. 9
   Extractionextracted three times with ether
10. 10
    AutreRemoval of the dried ether solution
11. 11
    Autregave a crude oil

Mode opératoire

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.

Source