TBAF tetrahydrofuran → HCID 66852696, compound

HRID 1668516Notes

Reaction equation

HRID 1668516 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:15]=[C:14]([CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:13]=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1>[N:19]1([CH2:18][CH2:17][CH2:16][C:14]2[N:15]=[C:10]([CH2:9][OH:8])[CH:11]=[CH:12][CH:13]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 66852447HCID 66852447, compound

Product 1

HCID 66852696HCID 66852696, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, to a solution of 760 mg of 4-{3-[6-(t-butyldimethylsilanyloxymethyl)pyridin-2-yl]propyl}morpholine in 4 mL of THF at ice temperature, 4.34 mL of a solution of TBAF/THF (1 mol/L) was added dropwise. After stirring the solution at room temperature for 2 hours, the solvent was removed, and the residue was purified by chromatography on silica gel (methylene chloride-ethanol=40:1) to give 495 mg of [6-(3-morpholin-4-ylpropyl)pyridin-2-yl]methanol.

Workup

  1. customthe solvent was removed
  2. customthe residue was purified by chromatography on silica gel (methylene chloride-ethanol=40:1)

Sources & evidence

ORD record
ord-5d6fab1b54774adb8c3bc1236ee1dfbe
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

Loading…