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

HRID 10408Notes

Reaction equation

HRID 10408 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.C1(C)C=CC(S(OCCC#C)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[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

Conditions

Temperature
85 °C

Procedure

To a sealed flask was added 2-(R)-methylpyrrolidine L-tartrate (21.1 g, 90 mmol), 3-butynyl p-toluenesulfonate (15.7 mL, 89 mmol), potassium carbonate powder (18.5 g, 134 mmol) and CH3CN (160 mL). The resulting mixture was heated to 85° C. for 24 hours and the reaction was monitored by GC for the complete consumption of the tosylate. The reaction mixture was cooled to room temperature and filtered the wet cake was washed with CH3CN (40 mL). The combined filtrate was used in the next step without further processing.

Workup

  1. customthe reaction was monitored by GC for the complete consumption of the tosylate
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered the wet cake
  4. washwas washed with CH3CN (40 mL)

Sources & evidence

ORD record
ord-aaf4f21a45734751b2c179840ecdc207
Source dataset
uspto-grants-2006_08
Patent number
US07094790B2

Reaction notes

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