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

HRID 1467304Notes

Reaction equation

HRID 1467304 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

4

Reactant 3

HCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrileHCID 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.

Workup

  1. customTo a microwave vial equipped with a stir bar
  2. customThe vial was sealed

Sources & evidence

ORD record
ord-132bf7ff0b5441878c395edc1c60daf3
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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