Hydrochloric Acid → (S)-2-(Pyrrolidin-2-yl)acetonitrile hydrochloride
Reaction equation
[C:1]([CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1C(OC(C)(C)C)=O)#[N:2].[ClH:16]>CO>[ClH:16].[NH:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[CH2:3][C:1]#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A solution of tert-butyl (S)-2-cyanomethylpyrrolidine-1-carboxylate (Intermediate 139, 13.0 g) in methanol (130 mL) and concentrated hydrochloric acid (13 mL) was stirred and heated at 40° C. overnight. After cooling, the mixture was concentrated under vacuum and the residue was diluted with toluene and reconcentrated. Ethanol (20 mL) was added and the resultant solid was collected by filtration and washed with hexane to give ((S)-pyrrolidin-2-yl)acetonitrile hydrochloride (8.0 g) as a white solid.
Workup
- temperatureAfter cooling
- concentrationthe mixture was concentrated under vacuum
- additionthe residue was diluted with toluene
- additionEthanol (20 mL) was added
- filtrationthe resultant solid was collected by filtration
- washwashed with hexane
Sources & evidence
- ORD record
- ord-b7812456ee8848e285e578d2e1c658e1
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290472B2
Reaction notes
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