hexahydro-5-oxo-1H-pyrrolizine-3-carboxylic acid ethyl ester → N-[N,N-diethylamino-ethyl]hexahydro-5-oxo-1H-pyrrolizine-3-carboxamide

HRID 980451Notes

Reaction equation

HRID 980451 reaction equation
C(O[C:4]([CH:6]1[N:13]2[CH:9]([CH2:10][CH2:11][C:12]2=[O:14])[CH2:8][CH2:7]1)=[O:5])C.C(N[N:18]([CH2:22][CH3:23])NCC)C>>[CH2:12]([N:13]([CH2:23][CH2:22][NH:18][C:4]([CH:6]1[N:13]2[CH:9]([CH2:10][CH2:11][C:12]2=[O:14])[CH2:8][CH2:7]1)=[O:5])[CH2:6][CH3:4])[CH3:11]

Participants

3

Reactant 2

HCID 13756031hexahydro-5-oxo-1H-pyrrolizine-3-carboxylic acid ethyl esterHCID 57254831N,N-diethylaminoethylamine

Product 1

HCID 20221658N-[N,N-diethylamino-ethyl]hexahydro-5-oxo-1H-pyrrolizine-3-carboxamide

Conditions

Temperature
80 °C

Procedure

A solution of hexahydro-5-oxo-1H-pyrrolizine-3-carboxylic acid ethyl ester (5.0 g, 0.0254 mol) in N,N-diethylaminoethylamine (23.2 g, 0.2 mol) is stirred at room temperature 24 hours and heated at 80° C. for 24 hours. The solution is concentrated at reduced pressure and distilled to yield N-[N,N-diethylamino-ethyl]hexahydro-5-oxo-1H-pyrrolizine-3-carboxamide

Workup

  1. concentrationThe solution is concentrated at reduced pressure
  2. distillationdistilled

Sources & evidence

ORD record
ord-96881b4ccff4409baee21829563a7e0a
Source dataset
uspto-grants-1987_01
Patent number
US04638006

Reaction notes

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