Triethylamine → 5-(1-Amino-2-cyclopropyl-ethylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione

HRID 1242522Notes

Reaction equation

HRID 1242522 reaction equation
Cl.CO[C:4](=[NH:9])[CH2:5][CH:6]1[CH2:8][CH2:7]1.[CH3:10][C:11]1([CH3:19])[O:16][C:15](=[O:17])[CH2:14][C:13](=[O:18])[O:12]1.C(N(CC)CC)C>C(Cl)(Cl)Cl.ClCCl>[NH2:9][C:4](=[C:14]1[C:15](=[O:17])[O:16][C:11]([CH3:19])([CH3:10])[O:12][C:13]1=[O:18])[CH2:5][CH:6]1[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 67072443Methyl 2-Cyclopropylacetimidate Hydrochloride

Product 1

HCID 219356625-(1-Amino-2-cyclopropyl-ethylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dioneYield 9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

1 g (7 mmol) 2-Cyclopropyl-acetimidic acid methyl ester hydrochloride, 963 mg (7 mmol) 2,2-dimethyl-[1,3]dioxane-4,6-dione and 1.07 ml (8 mmol) triethylamine were heated under reflux in 7 ml chloroform for 14 h. The mixture was diluted with dichloromethane, washed neutral with brine/ice water 1/1 and the organic layer was dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography (silica gel, heptane/AcOEt) to give 128 mg (0.6 mmol, 9%) of the title compound as yellow crystals.

Workup

  1. washwashed neutral with brine/ice water 1/1
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by flash chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-258d7064f52a4321bab9c31df02f9257
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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