Hydrochloric Acid → Methyl 1-(4-methoxybenzyl)-5-oxopyrrolidine-3-carboxylate

HRID 130522

Reaction equation

HRID 130522 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[C:11]([O:20][CH3:21])(=[O:19])[C:12]([CH2:14][C:15](OC)=[O:16])=[CH2:13].Cl.CCOCC>CO>[CH3:21][O:20][C:11]([CH:12]1[CH2:14][C:15](=[O:16])[N:8]([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:13]1)=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69240Dimethyl itaconateHCID 754524-Methoxybenzylamine

Product 1

HCID 4093874Methyl 1-(4-methoxybenzyl)-5-oxopyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 4-methoxybenzylamine (42 g, 0.306 mol) in methanol (40 mL) at 0° C. was added the dimethyl itaconate (48 g, 0.306 mol) in methanol (13 mL). The solution was stirred at room temperature for 4 days. 1N HCl was added to the solution followed by ether. The two layers were separated and the aqueous phase extracted with ether. The combined organic phases were dried (MgSO4). Upon filtration of the drying agent the desired material 79 precipitated from solution that was collected and dried under vacuum. 23.26 g, 29%. MS, m/z (relative intensity): 264 [M+H, 100%]. Anal. Calcd for C14H17N1O4: C, 63.87; H, 6.51; N, 5.32. Found: C, 63.96; H, 6.55; N, 5.29.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous phase extracted with ether
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationUpon filtration of the drying agent the desired material 79
  5. customprecipitated from solution that
  6. customwas collected
  7. customdried under vacuum

Sources & evidence

ORD record
ord-8aa5d35ff35e4167ac525a53fd4c1c0b
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Linked notes

Loading…