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

HRID 1824238Notes

Reaction equation

HRID 1824238 reaction equation
Cl.C[O:3][C:4](=O)[CH:5]([NH:9][C:10](=[O:14])[C@H:11]([CH3:13])[NH2:12])[CH:6]1[CH2:8][CH2:7]1>N.CO>[CH:6]1([CH:5]2[NH:9][C:10](=[O:14])[CH:11]([CH3:13])[NH:12][C:4]2=[O:3])[CH2:8][CH2:7]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-387ba09e09404805bb7e9bb6ba00a64b
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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