hexahydro-5-oxo-1H-pyrrolizine-3-carboxylic acid ethyl ester → N-[2-[N,N-bis(1-methylethyl)amino]ethyl]-hexahydro-5-oxo-1H-pyrrolizine3-carboxamide

HRID 980450Notes

Reaction equation

HRID 980450 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.CCCN[N:19]([CH2:24][CH3:25])NCCC>>[CH3:4][CH:6]([N:13]([CH2:25][CH2:24][NH:19][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])[CH:9]([CH3:10])[CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 13756031hexahydro-5-oxo-1H-pyrrolizine-3-carboxylic acid ethyl esterHCID 86741219N,N-di-(2-methylethyl)aminoethylamine

Product 1

HCID 13756032N-[2-[N,N-bis(1-methylethyl)amino]ethyl]-hexahydro-5-oxo-1H-pyrrolizine3-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-di-(2-methylethyl)aminoethylamine (10 g, 0.0693 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-[2-[N,N-bis(1-methylethyl)amino]ethyl]-hexahydro-5-oxo-1H-pyrrolizine3-carboxamide, bp 155°-165° C. at 0.025 Torr.

Workup

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

Sources & evidence

ORD record
ord-e5c393fb8fc64e0787fbf9d49dafc3d2
Source dataset
uspto-grants-1987_01
Patent number
US04638006

Reaction notes

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