Triethylamine → Oxolan-3-yl methanesulfonate

HRID 2066547Notes

Reaction equation

HRID 2066547 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>ClCCl>[O:1]1[CH2:5][CH2:4][CH:3]([O:6][S:15]([CH3:14])(=[O:17])=[O:16])[CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99603-Furanol, tetrahydro-HCID 31297Methanesulfonyl chloride

Product 1

HCID 15278452Oxolan-3-yl methanesulfonateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To tetrahydro-furan-3-ol (1.0 g, 11.4 mmol) in anhydrous dichloromethane (15 mL) with triethylamine (2.37 mL, 17.03 mmol), was added methane sulfonyl chloride (12.5 mmol) at 0° C. The reaction mixture was stirred at RT for 3.5 hours, diluted with dichloromethane (50 mL) and washed with water. The organic phase was dried (MgSO4) and evaporated in-vacuo to give methanesulfonic acid tetrahydro-furan-3-yl ester as light orange oil (1.68 g, 89%). A mixture of piperazine-1-carboxylic acid tert-butyl ester (1.0 g, 5.38 mmol), methanesulfonic acid tetrahydrofuran-3-yl ester (1.07 g, 6.45 mmol) and K2CO3 (2.96 g, 21.5 mmol) was stirred in anhydrous acetonitrile (50 mL) under reflux conditions for 12 hours. The reaction mixture was cooled and poured onto water and extracted with dichloromethane to give after silica chromatography, 4-(tetrahydro-furan-3-yl)-piperazine-1-carboxylic acid tert-butyl ester, as a colourless oil (0.57 g, 41%).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated in-vacuo

Sources & evidence

ORD record
ord-05c15dc7b1fa4f59a877e99419906cb1
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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