Water → 2-(n-Methyl-2-pyrrolidinyl)proprionitrile
Reaction equation
[C:1]([CH:4]1CCC[N:5]1[CH3:9])(=O)[CH3:2].C1(C)C(S(C[N+:20]#[C-])(=O)=O)=CC=CC=1.[CH3:23][C:24]([CH3:27])([O-])[CH3:25].[K+].O>COCCOC.C(O)(C)(C)C>[CH3:9][N:5]1[CH2:4][CH2:1][CH2:2][CH:23]1[CH:24]([CH3:27])[C:25]#[N:20]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
2-Acetyl-N-methylpyrrolidine 0.979g (7.7 mmol) and toluenesulfonylmethyl isocyanide 2.3 g (11.5 mmol) are dissolved in 50 mL of dry DME and cooled to −78° C. while stirring under N2. To this mixture is added dropwise a solution of potassium t-butoxide 1.75 g (15.4 mmol) in 15 mL of hot t-butanol. The reaction mixture is stirred at −78° C. for 3 h then poured into 50 mL of H2O and extracted with 150 mL of dichloromethane and 150 mL of EtOAc. The organic layers are combined, washed with saturated NaHCO3 and saturated NaCl, dried and concentrated in vacuo. Purification by chromatography gives the title compound.
Workup
- stirringThe reaction mixture is stirred at −78° C. for 3 h
- extractionextracted with 150 mL of dichloromethane and 150 mL of EtOAc
- washwashed with saturated NaHCO3 and saturated NaCl
- customdried
- concentrationconcentrated in vacuo
- customPurification by chromatography
Sources & evidence
- ORD record
- ord-1e4e6f94630f405eab3f03d38f7372f7
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06355655B1
Reaction notes
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