Potassium tert-butoxide → HCID 86629258, compound

HRID 1868808Notes

Reaction equation

HRID 1868808 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[C:26][Si](CC)(CC)CC)[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].CC(C)([O-])C.[K+]>CO>[CH2:12]([N:9]1[CH2:8][CH2:7][C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[CH:26])([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 67099455HCID 67099455, compound

Product 1

HCID 86629258HCID 86629258, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl-1-benzyl-4-(2-(2-(triethylsilyl)ethynyl)phenyl)-piperidine-4-carboxylate (0.50 g, 1.1 mmol) and MeOH (10 mL), was added potassium t-butoxide (0.15 g, 1.3 mmol). The reaction mixture was heated at 40° C. for 15 hours. The reaction mixture was then concentrated in vacuo and loaded on a silica gel column and purified by Isco HPLC (0-50% EtOAc/hexane) to give the title compound as a viscous light yellow oil (0.22 g). MS m/e=348 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompurified by Isco HPLC (0-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-652745953394473e99addc4320418509
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…