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ChemicalBook CAS DataBase List (S)-tert-butyl 2-(2-aminothiazol-4-yl)pyrrolidine-1-carboxylate
871716-68-6

(S)-tert-butyl 2-(2-aminothiazol-4-yl)pyrrolidine-1-carboxylate synthesis

2synthesis methods
(R)-tert-butyl 2-(2-chloroacetyl)pyrrolidine-1-carboxylate

871716-67-5
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Carbamimidothioic acid

17356-08-0
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(S)-tert-butyl 2-(2-aminothiazol-4-yl)pyrrolidine-1-carboxylate

871716-68-6
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Yield:-

Reaction Conditions:

in ethanol at 70; for 1 h;Sealed tube;Inert atmosphere;

Steps:



A 250 mL vial with stir bar was charged with tert-butyl (2R)-2-(2-chloroacetyl)pyrrolidine-1-carboxylate (5.00 g, 20.18 mmol, 1.00 equiv), thiourea (2.30 g, 30.22 mmol, 1.50 equiv) and EtOH (60.00 mL, 0.34 M) under nitrogen atmosphere. The vial was capped and placed in a 70°C bath. The reaction mixture was stirred at 70°C for 1 h. The reaction mixture was cooled to room temperature and concentrated under vacuum. The reaction mixture was then quenched by NaHCO3(aq). The resulting solution was extracted with DCM (3 x 50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude material was purified via silica gel chromatography to yield the desired product.

References:

WO2022/47347,2022,A1 Location in patent:Paragraph 00206