반응 #1125983

반응 방정식

benzyl 4-cyanopiperidine-1-carboxylate

LiHMDS

Paraformaldehyde

→

benzyl 4-cyano-4-(hydroxymethyl)piperidine-1-carboxylate

수율 41.0%

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred overnight at rt
2. 2
   농축The mixture was concentrated in vacuo
3. 3
   기타the residue was purified by preparative TLC (1:1 EtOAc/pet ether)

실험 절차

To a mixture of benzyl 4-cyanopiperidine-1-carboxylate (1.0 g, 4.0 mmol, Oakwood) in THF (50 mL) at about −78° C. was added LiHMDS (1.0 M solution in THF, 6.14 mL, 6.14 mmol) dropwise via syringe. The mixture was stirred for about 1 h. Paraformaldehyde (0.25 g, 8.2 mmol) was added in one portion and the mixture was stirred overnight at rt. The mixture was concentrated in vacuo and the residue was purified by preparative TLC (1:1 EtOAc/pet ether) to give benzyl 4-cyano-4-(hydroxymethyl)piperidine-1-carboxylate (0.45 g, 35%): LC/MS (Table 2, Method k) Rt=0.60 min; MS m/z: 274 (M+H)+.

출처