Cyclohexylamine → 1-Cyclohexyl-2-oxopyrrolidine-3-carboxylic acid

HRID 58546

Reaction equation

HRID 58546 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1(C)[O:16][C:15](=O)[C:12]2([CH2:14][CH2:13]2)[C:11](=[O:18])[O:10]1>C(O)C>[CH:1]1([N:7]2[CH2:14][CH2:13][CH:12]([C:11]([OH:18])=[O:10])[C:15]2=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 797206,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione

Product 1

HCID 242751731-Cyclohexyl-2-oxopyrrolidine-3-carboxylic acidYield 36.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cyclohexylamine (1.02 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 0.228 g (36%) of 1-cyclohexyl-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-ff334f9e31ef4c6dbfa93fb66370d353
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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