تفاعل #358530

معادلة التفاعل

cis-3-tert-butoxycarbonylmethyl-cyclobutanecarboxylic acid

N-methyl-piperidine

isobutyl chloroformate

N-methyl-N-methoxy-amine hydrochloride

→

product

المردود 99.5%

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

المردود 99.5%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm
2. 2
   غسيلwashed with 100 mL of water, 100 mL of 0.1 N HCl, 50 mL of saturated sodium carbonate
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   workup.ADDITIONThe solution was diluted with 50 mL of toluene
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىDrying under vacuum overnight

الإجراء التجريبي

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).

المصدر