Potassium Carbonate → (R)-1-(But-3-yn-1-yl)-2-methylpyrrolidine
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([CH:10]([CH:12]([C:14](O)=O)O)O)(O)=O.[CH3:17][C@@H:18]1[CH2:22][CH2:21][CH2:20][NH:19]1.CC1C=CC(S(OCCC#C)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O>C(#N)C>[CH2:7]([N:19]1[CH2:20][CH2:21][CH2:22][C@H:18]1[CH3:17])[CH2:10][C:12]#[CH:14]Participants
6
Conditions
- Temperature
- 85 °C
Procedure
A sealed pressure tube was charged potassium carbonate powder (18.4 g, 133.2 mmol, 325 mesh), milled (2R)-2-methylpyrrolidine tartrate (20.9 g, 88.8 mmol), 3-butynyl 4-methylbenzenesulfonate (15.7 mL, 88.8 mmol), and acetonitrile (105 mL). The mixture was heated at 85° C. and stirred for 16 hours. The completion of the reaction was monitored by gas chromatography until all the tosylate was consumed. The reaction mixture was cooled to room temperature, diluted with CH3CN (50 mL), and filtered. The filtrate was used in the next step without further purification. GC-MS m/z 138 (M+H)+.
Workup
- customwas consumed
- temperatureThe reaction mixture was cooled to room temperature
- additiondiluted with CH3CN (50 mL)
- filtrationfiltered
- customThe filtrate was used in the next step without further purification
Sources & evidence
- ORD record
- ord-71e563b75b9d4fe6afb0f5c7fcaeb362
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06822101B2
Reaction notes
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