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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2251449Generated: October 30, 2026

Potassium Cyanide → tert-butyl (3aR,6aR)-5-[6-bromo-5-(cyanomethyl)-3-pyridinyl]hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate

https://huagongshe.com/reaction/2251449

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CyanideHCID 9032—
ReactantHCID 86584384HCID 86584384—
SolventDimethylformamideHCID 6228—
Producttert-butyl (3aR,6aR)-5-[6-bromo-5-(cyanomethyl)-3-pyridinyl]hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylateHCID 8658438339%

Reaction Conditions

Temperature60 °C

Reaction Steps

The product of Example 66A (0.300 g, 0.630 mmol) in N,N-dimethylformamide (5 mL) was treated with KCN (61 mg, 0.945 mmol). The mixture was warmed to 60° C. and allowed to stir for 20 hours. The mixture was then concentrated under reduced pressure and the residue purified via chromatography (SiO2, 50% ethyl acetate/hexanes) to provide the title compound (0.100 g, 0.246 mmol, 39% yield). MS (DCI/NH3) m/z 409 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07319106B2
Source datasetuspto-grants-2008_01
ORD IDord-a464e73e061f4b1486e42342687a4b24
Source noteuspto-grants-2008_01