반응 #1126013

반응 방정식

NH4Cl

LiHMDS

benzyl 4-cyanopiperidine-1-carboxylate

Met

→

benzyl 4-cyano-4-methylpiperidine-1-carboxylate

수율 80.3%

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred overnight at rt
2. 2
   추출The mixture was extracted with DCM (3×300 mL)
3. 3
   건조The combined organic extracts were dried over anhydrous Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타purified by column chromatography
7. 7
   세척eluting with 10:1 pet ether/EtOAc

실험 절차

LiHMDS (47.6 mL, 47.6 mmol) was added dropwise via syringe to the mixture of benzyl 4-cyanopiperidine-1-carboxylate (8.00 g, 31.8 mmol, [Oakwood]) in THF (50 mL) at about −78° C. and stirred for about 1 h. Met (6.76 g, 47.6 mmol) was added dropwise via syringe at about −78° C. and the mixture was stirred overnight at rt. The solution was cooled to 0° C. and saturated aqueous NH4Cl (200 mL) was added. The mixture was extracted with DCM (3×300 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The sample was deposited onto silica gel and purified by column chromatography eluting with 10:1 pet ether/EtOAc to give benzyl 4-cyano-4-methylpiperidine-1-carboxylate (6.6 g, 74%): LC/MS (Table 2, Method i) Rt=2.03 min; MS m/z: 259 (M+H)+.

출처