Hydrochloric Acid → 4-(4-Nitro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

HRID 1266456Notes

Reaction equation

HRID 1266456 reaction equation
C(OC([N:6]1[CH2:10][CH:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH:8]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:7]1)=O)=C.Cl>O1CCOCC1>[CH2:23]([O:22][C:20]([CH:8]1[CH:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:10][NH:6][CH2:7]1)=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 538573774-(4-Nitro-phenyl)-pyrrolidine-1,3-dicarboxylic acid 3-ethyl ester 1-vinyl ester

Product 1

HCID 539414194-(4-Nitro-phenyl)-pyrrolidine-3-carboxylic acid ethyl esterYield 90.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of 4-(4-nitro-phenyl)-pyrrolidine-1,3-dicarboxylic acid 3-ethyl ester 1-vinyl ester (6 g, Reference Example 5) in dioxane (30 ml), at 25° C., was treated dropwise with hydrochloric acid (15 ml, 4N). After stirring for 2 hours the mixture was treated with a further aliquot of hydrochloric acid (15 ml, 4N) and stirring was continued at 25° C. for a further 2 hours. The reaction mixture was evaporated (40° C. and 2.7 kPa) and the residue was heated at reflux temperature with ethanol (30 ml) for 45 minutes. The mixture was cooled to room temperature then evaporated and the residue was triturated with diethyl ether (100 ml) for 20 hours affording the title compound (4.3 g) as a white solid. TLC: RF=25/70 [on silica plates eluting with a mixture of dichloromethane and methanol, (90:10, v/v)]. 1H-NMR [400 MHz, (CD3)2SO]: δ 1.09 (t, J=7 Hz, 3H); 3.25 to 3.85 (3 m, 6H); 4.05 (m, 2H); 7.76 (d, J=8.5 Hz, 2H); 8.24 (d, J=8.5 Hz, 2H); 9.90 (b, 2H). MS (EI): 264[M]+.

Workup

  1. stirringstirring
  2. waitwas continued at 25° C. for a further 2 hours
  3. customThe reaction mixture was evaporated (40° C. and 2.7 kPa)
  4. temperaturethe residue was heated
  5. temperatureat reflux temperature with ethanol (30 ml) for 45 minutes
  6. customthen evaporated
  7. customthe residue was triturated with diethyl ether (100 ml) for 20 hours

Sources & evidence

ORD record
ord-d39455f7bd084daa97494dbc176b0c67
Source dataset
uspto-grants-2003_04
Patent number
US06548533B2

Reaction notes

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