تفاعل #2286356

ord-263ff533434f4b51bb74d41ff2e49cb2

معادلة التفاعل

[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

ظروف التفاعل

درجة الحرارة
-78°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09357779B2uspto-grants-2016_06