Ethyl cyanoacetate → 1-(Cyanoacetyl)pyrrolidine

Reaction equation

[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>>[O:6]=[C:4]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[CH2:3][C:1]#[N:2]

Participants

Reactant 2

HCID 7764Ethyl cyanoacetate

HCID 31268Pyrrolidine

Product 1

HCID 842721-(Cyanoacetyl)pyrrolidineYield 72.4%

Procedure

Ethyl cyanoacetate (5.33 mL, 50 mmol) and pyrrolidine (20.87 mL, 250 mmol) were gently refluxed at 90° C. in an oil bath for 8 hours. Excess pyrrolidine was removed by concentration and the residue was triturated with diethyl ether. This was purified by silica gel column chromatography eluting with 50% acetone in n-hexane to provide the desired product (5.0 g). MS (DCI) m/e 139 (M+H)+, 156 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 3.90 (s, 2H), 3.27-3.38 (m, 4H), 1.73-1.91 (m, 4H).

Workup

customExcess pyrrolidine was removed by concentration
customthe residue was triturated with diethyl ether
customThis was purified by silica gel column chromatography
washeluting with 50% acetone in n-hexane

Sources & evidence

ORD record: ord-36d6b918c95a40108c255e7d5d65b832
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491718B2

Reaction notes

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