Ethanol → Ethyl pyrrolidine-3-carboxylate

HRID 926704Notes

Reaction equation

HRID 926704 reaction equation
S(Cl)(Cl)=O.[NH:5]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[CH2:6]1.[CH3:13][CH2:14]O>>[NH:5]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 30346453-Pyrrolidinecarboxylic acid

Product 1

HCID 12896002Ethyl pyrrolidine-3-carboxylate

Conditions

Temperature
80 °C

Procedure

Thionyl chloride (5 mL) was added to a cold (0° C.) stirred solution of pyrrolidine-3-carboxylicacid (500 mg, 4.34 mmol) in EtOH (25 mL) and continued stirring at 80° C. for 12-16 h. The reaction mixture was concentrated under reduced pressure to afford 600 mg (crude) of ethyl pyrrolidine-3-carboxylate, which was used as such in the next step without purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2428d09e5bfc4063aa5d2c18594791cd
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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