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

HRID 1527848Notes

Reaction equation

HRID 1527848 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-34633c2a02b44323973fdde89032f83d
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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