Potassium Carbonate → tert-Butyl (R)-(1-(2-cyanobenzyl)piperidin-3-yl)carbamate

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[C:25]#[N:26]>>[C:25]([C:24]1[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=1[CH2:22][N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:2]1)#[N:26]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 895992-(Bromomethyl)benzonitrile

HCID 1514172(3R)-3-Aminopiperidine, 3-BOC protected

Product 1

HCID 70652603tert-Butyl (R)-(1-(2-cyanobenzyl)piperidin-3-yl)carbamate

Procedure

To a microwave vial equipped with a stir bar was added tert-butyl (3R)-piperidin-3-ylcarbamate (3000 mg, 14.98 mmol), Potassium Carbonate (6211 mg, 44.9 mmol), and 2-(bromomethyl)benzonitrile (3230 mg, 16.48 mmol). The vial was sealed and stirred at room temperature. The LCMS taken after 2.5 hours indicates the formation of the desired product. The crude reaction mixture was filtered and concentrated in vacuo. The material was dry loaded onto a 50 g column. The column was run from 100% dichloromethane to 15% methanol. The desired product eluted and the fractions were collected and concentrated in vacuo.