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

HRID 890486Notes

Reaction equation

HRID 890486 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

2-Cyclopropyl-acetimidic acid methyl ester hydrochloride (1 g, 7 mmol), 2,2-dimethyl-[1,3]dioxane-4,6-dione (963 mg, 7 mmol) and triethylamine (1.07 ml, 8 mmol) in chloroform (7 ml) were heated under reflux conditions 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-01f5cfb3901243888dd892b6d01aed25
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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