Potassium Cyanide → (S)-Benzyl 3-cyanopyrrolidine-1-carboxylate

HRID 50135

Reaction equation

S([C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12]1)(C1C=CC(C)=CC=1)(=O)=O.[C-:26]#[N:27].[K+].[Cl-].[Na+].O.O>CS(C)=O>[C:26]([C@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:12]1)#[N:27]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Tosyl-Cbz-(R)-pyrrolidine (20.4 g, 0.05 mol) was dissolved in DMSO (54 mL), followed by the addition of KCN (5.3 g, 0.08 mol). The reaction mixture was stirred for 5 h at 80° C. The solution was cooled to room temperature and brine/H2O (90 mL) (1/1, v/v) was added. The aqueous solution was extracted with ethyl acetate. The organic extracts were dried over MgSO4, and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate/hexanes (1/1, v/v) to afford 8.13 g (65% yield) of the desired product as an oil.

Workup

temperatureThe solution was cooled to room temperature
extractionThe aqueous solution was extracted with ethyl acetate
dry with materialThe organic extracts were dried over MgSO4
concentrationconcentrated
customThe crude product was purified by column chromatography
washeluting with ethyl acetate/hexanes (1/1

Sources & evidence

ORD record: ord-2ac083ed0182438fba7129a72c857851
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710186B2

Linked notes

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