反应 #2286356

ord-263ff533434f4b51bb74d41ff2e49cb2

反应方程式

[Cl][Mg][CH2]C1CCCCC1
cyclohexylmethylmagnesium chloride
CON(C)C(=O)c1csc(C2CCN(C(=O)OC(C)(C)C)CC2)n1
tert-butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate
[Cl-].[NH4+]
ammonium chloride
CC(C)(C)OC(=O)N1CCC(c2nc(C(=O)CC3CCCCC3)cs2)CC1
tert-Butyl 4-[4-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

反应条件

温度
-78°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

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

实验过程

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).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US09357779B2uspto-grants-2016_06