Hydrogen Peroxide → 2,3-Diaza-spiro[4.4]non-2-ene

C-(1-Aminomethyl-cyclopentyl)-methylamine (4.87 g) was taken up in a mixture of H2O (40 mL) and MeOH (10 mL), and cooled in an ice bath. Simultaneously, H2O2 (23.9 mL of a 30% solution. 6 equiv.) and NaClO (54.3 mL of a 10% solution, 2.4 equiv.) were added dropwise, the ice bath was removed, and the mixture was stirred for 2 h. at room temperature. Extraction with DCM, drying over Na2SO4 and evaporation under reduced pressure yielded 3.74 g of a clear, light-yellow liquid containing 90% of the anticipated product and 10% of the diamine starting material. This material was used in subsequent steps without further purification. 1H NMR (400 MHz, CDCl3) δ 1.48-1.57 (m, 4H), 1.62-1.69 (m, 4H), 4.26 (s, 4H).

1. temperaturecooled in an ice bath
2. customthe ice bath was removed
3. extractionExtraction with DCM
4. dry with materialdrying over Na2SO4 and evaporation under reduced pressure
5. customyielded 3.74 g of a clear, light-yellow liquid

ORD-Eintrag

ord-950943709ef94e2cbd449c048cfa7060

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07728018B2