반응 #8840

반응 방정식

sodium bicarbonate

potassium bis(trimethylsilyl)amide

methyl 1-(tert-butoxycarbonyl)piperidine-4-carboxylate

Methyl 1-(tert-butoxycarbonyl)piperidine-4-carboxylate

5-Bromo-1-pentene

→

title compound

수율 99.2%

Methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

수율 99.2%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   추출extracted three times with ethyl acetate
2. 2
   세척washed with brine
3. 3
   건조dried over sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated

실험 절차

To a solution of potassium bis(trimethylsilyl)amide (30.7 g, 0.15 mol) in tetrahydrofuran (750 mL) at 0° C. was added a solution of methyl 1-(tert-butoxycarbonyl)piperidine-4-carboxylate (25 g, 0.10 mol) from Step A in tetrahydrofuran (250 mL) and the reaction mixture was stirred for 1 h. 5-Bromo-1-pentene (19.4 mL, 0.164 mol) was added and the reaction mixture was allowed to warm to room temperature for 1.5 h. The reaction mixture was then poured into saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the title compound (30.9 g) which was used in the next step without further purification.

출처