Benzylamine → 1-Benzyl-2-oxopyrrolidine-3-carboxylic acid

HRID 58544

Reaction equation

HRID 58544 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)[O:17][C:16](=O)[C:13]2([CH2:15][CH2:14]2)[C:12](=[O:19])[O:11]1>C(O)C>[CH2:1]([N:8]1[CH2:15][CH2:14][CH:13]([C:12]([OH:19])=[O:11])[C:16]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 797206,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione

Product 1

HCID 225602101-Benzyl-2-oxopyrrolidine-3-carboxylic acidYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of benzylamine (0.962 mL; 8.82 mmol) and 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (0.5 g; 2.94 mmol) in ethanol (3 mL) was irradiated in a microwave oven for 3 minutes at 100° C. and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 30 to 100% ethyl acetate in heptane with 5% acetic acid) to afford 0.512 g (79%) of 1-benzyl-2-oxopyrrolidine-3-carboxylic acid.

Workup

  1. customwas irradiated in a microwave oven for 3 minutes at 100° C.
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by flash chromatography on silica gel (eluent 30 to 100% ethyl acetate in heptane with 5% acetic acid)

Sources & evidence

ORD record
ord-47e32a052bee478a8c27bdc567aa915c
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

Loading…