Реакция #1138147

Уравнение реакции

4-(4-methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

diethylsilane

hydrochloric acid

→

4-(4-formyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеthe mixture is irradiated in a microwave reactor for 1.5 hours at 50° C
2. 2
   ДругоеThe organic layer is separated
3. 3
   Сушкаdried over sodium sulfate
4. 4
   Другоеevaporated
5. 5
   ДругоеThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Методика

To a solution of 4-(4-methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (776 mg, 2.43 mmol) in dichloromethane (10 ml) are added diethylsilane (470 μl, 3.64 mmol) and chlorobis(cyclooctene)iridium(I) dimer (22 mg, 0.025 mmol) and the mixture is irradiated in a microwave reactor for 1.5 hours at 50° C. The reaction mixture is stirred vigorously with 2 N hydrochloric acid (0.6 ml) for 30 minutes. The organic layer is separated, dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 4-(4-formyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester as yellow resin; HPLC/MS 2.10 min (A), [M-tBu] 234.

Источник