반응 #616293

반응 방정식

(5R,7R)-4-(1′-benzyl-4-((tert-butoxycarbonylamino)methyl)spiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate

1-chloroethyl carbonochloridate

→

(5R,7R)-4-(4-((tert-butoxycarbonylamino)methyl)spiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for 1 h
3. 3
   기타evaporated in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in MeOH (1 mL)
5. 5
   온도the mixture was heated
6. 6
   온도at reflux for 1 h
7. 7
   온도After cooling
8. 8
   기타the solvent was evaporated in vacuo

실험 절차

To a stirred solution of (5R,7R)-4-(1′-benzyl-4-((tert-butoxycarbonylamino)methyl)spiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (30 mg, 0.043 mmol) in toluene (1 mL) was added 1-chloroethyl carbonochloridate (0.009 mL, 0.08 mmol) at about 0° C. The reaction mixture was heated at reflux for 1 h and then evaporated in vacuo. The residue was dissolved in MeOH (1 mL) and the mixture was heated at reflux for 1 h. After cooling, the solvent was evaporated in vacuo to give crude (5R,7R)-4-(4-((tert-butoxycarbonylamino)methyl)spiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate, which was used in the next step without further purification. LCMS (APCI+) m/z 615 [M+H]+; Rt=3.31 min.

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