methyl(L-alanylamino)(cyclopropyl)acetate hydrochloride → 3-Cyclopropyl-6-methylpiperazine-2,5-dione

HRID 1612323Notes

Reaction equation

HRID 1612323 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([NH:7][CH:8]([CH:13]1[CH2:15][CH2:14]1)[C:9](OC)=[O:10])=[O:6])[CH3:4]>N.CO>[CH:13]1([CH:8]2[NH:7][C:5](=[O:6])[CH:3]([CH3:4])[NH:2][C:9]2=[O:10])[CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 86588880methyl(L-alanylamino)(cyclopropyl)acetate hydrochloride

Product 1

HCID 221473683-Cyclopropyl-6-methylpiperazine-2,5-dioneYield 128.7%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of methyl (L-alanylamino)(cyclopropyl)acetate hydrochloride (230 mg, 0.97 mmol) in 7 N NH3 in MeOH (6 mL) was heated at reflux for 5 hr. Cool to rt and concentrate. The resulting material was dried at rt/0.5 mm Hg to provide 0.21 g of 3-cyclopropyl-6-methylpiperazine-2,5-dione as a solid: 1H NMR (CDCl3) δ 0.26-0.51, 1.06-1.37, 3.16-3.25, 3.50, 3.80, 4.00, 8.13.

Workup

  1. temperatureat reflux for 5 hr
  2. concentrationconcentrate
  3. customThe resulting material was dried at rt/0.5 mm Hg

Sources & evidence

ORD record
ord-b1f2a51d83e8432085c2e57b7c701bc8
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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