Reaction #2286356

Reaction equation

cyclohexylmethylmagnesium chloride

tert-butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

ammonium chloride

→

tert-Butyl 4-[4-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

Solvents

diethyl ether

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was then stirred at room temperature for one hour
2. 2
   Otherthe aqueous phase was separated off
3. 3
   ExtractionAfter extraction of the aqueous phase with ethyl acetate
4. 4
   Dryingthe combined organic phases were dried over sodium sulphate
5. 5
   Otherthe solvent was removed under reduced pressure

Procedure

Under argon and at −78° C., cyclohexylmethylmagnesium chloride 0.5M in diethyl ether (2.7 ml) was added dropwise to a solution of tert-butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (480 mg) in tetrahydrofuran (5 ml). The reaction mixture was stirred at −78° C. for one hour. The reaction mixture was then stirred at room temperature for one hour. Saturated ammonium chloride solution was then added to the reaction mixture, and the aqueous phase was separated off. After extraction of the aqueous phase with ethyl acetate, the combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. This gave tert-butyl 4-[4-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (335 mg).

Source