Реакция #358530

Уравнение реакции

cis-3-tert-butoxycarbonylmethyl-cyclobutanecarboxylic acid

N-methyl-piperidine

isobutyl chloroformate

N-methyl-N-methoxy-amine hydrochloride

→

product

Выход 99.5%

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

Выход 99.5%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Температураto warm
2. 2
   Промывкаwashed with 100 mL of water, 100 mL of 0.1 N HCl, 50 mL of saturated sodium carbonate
3. 3
   Сушкаdried over magnesium sulfate
4. 4
   workup.ADDITIONThe solution was diluted with 50 mL of toluene
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеDrying under vacuum overnight

Методика

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).

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