Reacción #358530

Ecuación de reacción

cis-3-tert-butoxycarbonylmethyl-cyclobutanecarboxylic acid

N-methyl-piperidine

isobutyl chloroformate

N-methyl-N-methoxy-amine hydrochloride

→

product

Rendimiento 99.5%

cis-[3-(Methoxy-methyl-carbamoyl)-cyclobutyl]-acetic acid tert-butyl ester

Rendimiento 99.5%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm
2. 2
   Lavadowashed with 100 mL of water, 100 mL of 0.1 N HCl, 50 mL of saturated sodium carbonate
3. 3
   Secadodried over magnesium sulfate
4. 4
   workup.ADDITIONThe solution was diluted with 50 mL of toluene
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroDrying under vacuum overnight

Procedimiento

To an ice cold solution of 1.74 g of cis-3-tert-butoxycarbonylmethyl-cyclobutanecarboxylic acid, 3 mL of N-methyl-piperidine, and 50 mL of dichloromethane was added 1.7 mL of isobutyl chloroformate drop-wise over 5 min. After an additional 5 min, 1.6 g of N-methyl-N-methoxy-amine hydrochloride was added and the mixture allowed to warm with stirring overnight. The resulting mixture was diluted with 100 mL of dichloromethane, washed with 100 mL of water, 100 mL of 0.1 N HCl, 50 mL of saturated sodium carbonate and dried over magnesium sulfate. The solution was diluted with 50 mL of toluene and concentrated under reduced pressure. Drying under vacuum overnight gave 2.08 g of product as a colorless thick oil: MS (m+1)=258.3; 1H NMR (400 MHz, CDCl3) 3.62 (s, 3H), 3.16 (s, 3H), 2.35 (d, 2H), 2.0 (dd, 1H), 1.4 (s, 9H).

Fuente