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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1500288Generated: November 1, 2026

Potassium Cyanide → (4S,5R)-tert-butyl 5-(4-(3-(cyanomethyl)isoxazol-5-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidine-3-carboxylate

https://huagongshe.com/reaction/1500288

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CyanideHCID 9032—
Reactant18-Crown-6HCID 28557—
Reactant(4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-((methylsulfonyloxy)methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylateHCID 86695496—
SolventAcetonitrileHCID 6342—
Product(4S,5R)-tert-butyl 5-(4-(3-(cyanomethyl)isoxazol-5-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidine-3-carboxylateHCID 8671317555.8%

Reaction Steps

The product of step 1 of Example 10 (200 mg, 0.41 mmol), potassium cyanide (111 mg, 1.65 mmol), and 18-crown-6 (23 mg, 0.08 mmol) in acetonitrile (8 mL) are stirred at room temperature for 16 hours then the mixture is concentrated and purified by column chromatography on silica gel eluting with a gradient of ethyl acetate/heptane to afford the title compound (95 mg). m/z (Cl) 416 [M+H].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09206126B2
Source datasetuspto-grants-2015_12
ORD IDord-05453c7bac654ad99ea9f063de72bb05
Source noteuspto-grants-2015_12