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

HRID 12480

반응식

HRID 12480 반응식
[NH2:1][CH2:2][C:3]1([CH2:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.OO.[O-]Cl.[Na+]>O.CO>[CH2:2]1[C:3]2([CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:8][N:9]=[N:1]1

참가 물질

6

반응물 3

HCID 784Hydrogen PeroxideHCID 4325931,1-CyclopentanedimethanamineHCID 23665760Sodium Hypochlorite

생성물 1

HCID 547519672,3-Diaza-spiro[4.4]non-2-ene수율 90%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-950943709ef94e2cbd449c048cfa7060
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728018B2

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