Water → (S)-2-(1-Acetylpyrrolidin-2-yl)acetonitrile
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[C:1](Cl)(=[O:3])[CH3:2].Cl.[NH:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][C:12]#[N:13].C(N(CC)CC)C.O>C(Cl)Cl>[C:1]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][C:12]#[N:13])(=[O:3])[CH3:2][C:1](Cl)(=[O:3])[CH3:2].Cl.[NH:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][C:12]#[N:13].C(N(CC)CC)C.O>C(Cl)Cl>[C:1]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][C:12]#[N:13])(=[O:3])[CH3:2]Acetyl chloride (8.6 g) was added dropwise to a stirred, cooled solution of ((S)-pyrrolidin-2-yl)acetonitrile hydrochloride (Intermediate 138, 8.0 g) and triethylamine (16.5 g) in DCM (80 mL) while maintaining the temperature at 0° C. The resultant solution was stirred at 0° C. for 30 minutes. Water was added and the layers were separated. The aqueous layer was further extracted with DCM and the combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by HPLC (C18) to give ((S)-1-acetylpyrrolidin-2-yl)acetonitrile (5.0 g) as a light yellow oil which was used directly without further characterisation.
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