تفاعل #2286363

ord-c73e0e36ba5b47f18e1ba6317e3a937b

معادلة التفاعل

CC(C)(C)OC(=O)N1CCC(c2nc(C=O)cs2)CC1
tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COP(=O)(OC)C(=[N+]=[N-])C(C)=O
dimethyl 1-diazo-2-oxopropylphos-phonate
C#Cc1csc(C2CCN(C(=O)OC(C)(C)C)CC2)n1
tert-Butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylate

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصAfter aqueous work-up, the mixture was extracted with ethyl acetate
  2. 2
    تجفيفthe extracts were dried with sodium sulphate
  3. 3
    تركيزthe solvent was concentrated under reduced pressure
  4. 4
    أخرىThe residue was purified chromatographically

الإجراء التجريبي

Under argon, tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (600 mg) was dissolved in methanol, and potassium carbonate (839 mg) and dimethyl 1-diazo-2-oxopropylphos-phonate (786 mg) were added. The mixture was stirred at room temperature for 3 hours. After aqueous work-up, the mixture was extracted with ethyl acetate, the extracts were dried with sodium sulphate and the solvent was concentrated under reduced pressure. The residue was purified chromatographically. This gave tert-butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (493 mg).

المصدر

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