ChemicalBook CAS DataBase List 1-CYANOCYCLOBUTANECARBOXYLIC ACID ETHYL ESTER

1-CYANOCYCLOBUTANECARBOXYLIC ACID ETHYL ESTER synthesis

4synthesis methods

Product Name:1-CYANOCYCLOBUTANECARBOXYLIC ACID ETHYL ESTER
CAS Number:28246-87-9
Molecular formula:C8H11NO2
Molecular Weight:153.18

4-(9>-cyclopentyl-5'-methyl-6>-oxo-5>,6>,8>,9>- tetrahydrospiro[cyclobutane-l,7'-pyrimido[4,5-b][l,4]diazepine]-2'-ylamino)-3- methoxybenzoic acid; [0521] Ethyl 1-cyanocyclobutanecarboxylate; To a solution of sodium ethoxide (21wt% in EtOH, 5.79 rnL, 15.5 mmol) in EtOH (25 mL), was added ethyl cyanoacetate(1.12 mL, 10.5 mmol), followed shortly thereafter by 1,1-dibromopropane (1.12 mL, 10 mmol). The reaction mixture was refluxed for 3 hrs. It was then concentrated, and diluted to ethyl acetate. The organic layer was washed with NaHCCh, brine, water, dried over Na2SO4 and concentrated in vacuo to obtain ethyl 1-cyanocyclobutanecarboxylate (1.17 g, 74% yield) as a red liquid. It was used directly for next step reaction.

105-56-6
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109-64-8 Synthesis

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1-CYANOCYCLOBUTANECARBOXYLIC ACID ETHYL ESTER

28246-87-9
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Yield:28246-87-9 74%

Reaction Conditions:

with sodium ethanolate in ethanol; for 3 h;Heating / reflux;

Steps:

178

Compound 178: 4-(9^>-cyclopentyl-5'-methyl-6^>-oxo-5^>,6^>,8^>,9^>- tetrahydrospiro[cyclobutane-l,7'-pyrimido[4,5-b][l,4]diazepine]-2'-ylamino)-3- methoxybenzoic acid; [0521] Ethyl 1-cyanocyclobutanecarboxylate; To a solution of sodium ethoxide (21wt% in EtOH, 5.79 rnL, 15.5 mmol) in EtOH (25 mL), was added ethyl cyanoacetate(1.12 mL, 10.5 mmol), followed shortly thereafter by 1,1-dibromopropane (1.12 mL, 10 mmol). The reaction mixture was refluxed for 3 hrs. It was then concentrated, and diluted to ethyl acetate. The organic layer was washed with NaHCCh, brine, water, dried over Na₂SO₄ and concentrated in vacuo to obtain ethyl 1-cyanocyclobutanecarboxylate (1.17 g, 74% yield) as a red liquid. It was used directly for next step reaction. ¹H NMR (400 MHz, CHLOROFORM- d) δ 1.32 (t, J=7.2 Hz, 3 H) 2.10 - 2.32 (m, 2 H) 2.59 - 2.76 (m, 4 H) 4.28 (q, J=7. I Hz, 3 H).

References:

WO2009/67547,2009,A1 Location in patent:Page/Page column 281-282