Tetrabutylammonium Fluoride → 3-Ethynyl-5-(pyrrolidin-1-ylmethyl)pyridine

HRID 1255917Notes

Reaction equation

HRID 1255917 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[N:9][CH:10]=[C:11]([C:13]#[C:14][Si](C)(C)C)[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:13]([C:11]1[CH:10]=[N:9][CH:8]=[C:7]([CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:12]=1)#[CH:14]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 212559323-(Pyrrolidin-1-ylmethyl)-5-[(trimethylsilyl)ethynyl]pyridine

Product 1

HCID 212559433-Ethynyl-5-(pyrrolidin-1-ylmethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(pyrrolidin-1-ylmethyl)-5-[(trimethylsilyl)ethynyl]pyridine (0.7 mmol) in 3.5 mL of THF is added 1.05 mL (1.05 mmol) of tetrabutylammonium fluoride (1.0M in THF) at ambient temperature. The solution is stirred for 15 min, concentrated, and the crude product is purified by silica gel flash chromatography (eluted with 50% EtOAc/hexanes) to provide product.

Workup

  1. concentrationconcentrated
  2. customthe crude product is purified by silica gel flash chromatography (eluted with 50% EtOAc/hexanes)
  3. customto provide product

Sources & evidence

ORD record
ord-3dd759434a5447d091657b7d64db38ac
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

Loading…