Reaktion #2144440

Reaktionsgleichung

trans-Methanesulfonic acid 3-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyl]-prop-2-ynyl ester

N-allylmethylamine

DMA

→

trans-{4-[3-(Allyl-methyl-amino)-prop-1-ynyl]-cyclohexyl}-methyl-carbamic acid tert-butyl ester

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe solution was concentrated
2. 2
   Extraktionthe residual oil was extracted with aqueous sat. NaHCO3/Et2O (3×)
3. 3
   WaschenThe organic phases were washed with aqueous 10% NaCl solution
4. 4
   Trocknendried over Na2SO4

Vorschrift

A solution of 420 mg (1.22 mmol) of trans-Methanesulfonic acid 3-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyl]-prop-2-ynyl ester in 4 ml DMA was treated at 0° C. with 0.234 ml (2.43 mmol) of N-allylmethylamine and stirred at RT for 16 h. The solution was concentrated and the residual oil was extracted with aqueous sat. NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl solution and dried over Na2SO4 to yield after flash column chromatography on silica gel with hexane/EtOAc (2:1) 355 mg (91%) trans-{4-[3-(Allyl-methyl-amino)-prop-1-ynyl]-cyclohexyl}-methyl-carbamic acid tert-butyl ester, MS: 321 (MH+).

Quelle