반응 #685024

반응 방정식

benzyl 4-cyanopiperidine-1-carboxylate

iodo-tert-butyldimethylsilane butane

THF

LiHMDS

→

title compound

수율 67.0%

Benzyl 4-(4-(tert-butyldimethylsilyloxy)butyl)-4-cyanopiperidine-1-carboxylate

수율 67.0%

반응 조건

후처리

1. 1
   기타After quenching with water
2. 2
   workup.ADDITIONthe organic phase was diluted with EtOAc
3. 3
   세척washed with water, brine
4. 4
   건조dried (Na2SO4)
5. 5
   농축After concentration
6. 6
   기타the residue was purified by flash chromatography (10% to 20% EtOAc/hexane)

실험 절차

To a stirred solution of benzyl 4-cyanopiperidine-1-carboxylate (10 g, 41 mmol) and iodo-tert-butyldimethylsilane butane (12.6 mL, 49 mmol) in THF (80 mL) cooled to −78° C. was added LiHMDS (50 mL, 50 mmol, 1M in THF) dropwise over 30 min. The resulting mixture was stirred while gradually warming to room temperature for 18 h. After quenching with water, the organic phase was diluted with EtOAc and washed with water, brine and dried (Na2SO4). After concentration, the residue was purified by flash chromatography (10% to 20% EtOAc/hexane) to give the title compound as yellow oil (11.88 g, 67% yield). 1H NMR (300 MHz, CDCl3) δ: 7.34-7.28 (5H, m), 5.09 (2H, s), 4.17 (2H, bs), 3.59 (2H, t, J=5.3 Hz), 3.07 (2H, bs), 1.89 (2H, d, J=13.2 Hz), 1.53 (6H, bs), 1.43-1.34 (2H, m), 0.85 (9H, s), 0.01 (6H, s). LCMS (M+H): 431.20.

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