Potassium Carbonate → (R)-1-(But-3-yn-1-yl)-2-methylpyrrolidine

HRID 494819Notes

Reaction equation

HRID 494819 reaction equation
[C:1]([C@@H:4]([C@H:6]([C:8](O)=O)O)O)(O)=O.[CH3:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.C([O-])([O-])=O.[K+].[K+].CC1C=CC(S(OCCC#C)(=O)=O)=CC=1>C(#N)C>[CH2:1]([N:13]1[CH2:14][CH2:15][CH2:16][C@H:12]1[CH3:11])[CH2:4][C:6]#[CH:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2720203-Butynyl p-toluenesulfonateHCID 11858493(R)-2-methylpyrrolidine L-tartrate

Product 1

HCID 11367023(R)-1-(But-3-yn-1-yl)-2-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-2-methylpyrrolidine (L) tartrate (1.65 g, 7.00 mmol) and 325 mesh powdered K2CO3 (2.03 g, 14.7 mmol) in acetonitrile (60 mL) were heated at 50° C. in a sealed bottle for 24 hours. The mixture was allowed to cool to room temperature and was treated with 3-butynyl 4-methylbenzenesulfonate (1.24 mL, 7.0 mmol). The mixture was stirred for one hour at room temperature and then was heated at 50° C. for 24 hours. The mixture was allowed to cool to room temperature, filtered, and the filter cake washed with acetonitrile. The filtrate was diluted to a total volume of 70 mL with acetonitrile and used as a 0.1M solution in subsequent steps.

Workup

  1. temperaturewas heated at 50° C. for 24 hours
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. washthe filter cake washed with acetonitrile
  5. additionThe filtrate was diluted to a total volume of 70 mL with acetonitrile

Sources & evidence

ORD record
ord-9a063880eded4b8f8b0c8d4ddfc08f59
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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