Ethanol → 2-Ethoxycarbonimidoyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1170510Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]#[N:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([OH:20])[CH3:19]>C(OCC)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]([O:20][CH2:18][CH3:19])=[NH:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -20 °C

Procedure

2-Cyano-pyrrolidine-1-carboxylic acid benzyl ester (17.0 g, 73.9 mmol) was dissolved in diethyl ether (100 mL). Ethanol (20.4 g, 444 mmol) was added and gaseous HCl was bubbled through the reaction mixture, while maintaining the temperature at −20° C. The temperature was maintained for 12 hours while stirring. The reaction mixture was concentrated under vacuo to afford 22.0 g (95%) of 2-ethoxycarbonimidoyl-pyrrolidine-1-carboxylic acid benzyl ester as a red oil.

Workup

customgaseous HCl was bubbled through the reaction mixture
temperatureThe temperature was maintained for 12 hours
concentrationThe reaction mixture was concentrated under vacuo

Sources & evidence

ORD record: ord-3c1b70ddfec64962a74f725da1d226c4
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825256B2

Reaction notes

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