Methyl morpholine oxide → 3-(5,6,7,8,9,10-Hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)-3-(2-thienyl)cyclobutanone

HRID 502985Notes

Reaction equation

HRID 502985 reaction equation
[N:1]1[N:2]=[C:3]([C:12]2([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH2:15][CH:14]([OH:16])[CH2:13]2)[N:4]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]=12.C[N+]1([O-])CCOCC1>C(Cl)Cl>[N:1]1[N:2]=[C:3]([C:12]2([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH2:13][C:14](=[O:16])[CH2:15]2)[N:4]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]=12

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 590064423-(5,6,7,8,9,10-Hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)-3-(2-thienyl)cyclobutanol

Product 1

HCID 684665703-(5,6,7,8,9,10-Hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)-3-(2-thienyl)cyclobutanoneYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)-3-(2-thienyl)cyclobutanol (2.73 g) was dissolved in methylene chloride (330 ml) and then tetra-n-propylammonium perruthenate(VII) (316 mg) and NMO (1.58 g) were added thereto, followed by stirring at room temperature for 15 hours. The reaction solution was subjected to evaporation under reduced pressure and the resulting residue was purified by column chromatography (methanol:chloroform=3:97) to obtain 2.16 g of 3-(5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)-3-(2-thienyl)cyclobutanone (pale yellow solid).

Workup

  1. customThe reaction solution was subjected to evaporation under reduced pressure
  2. customthe resulting residue was purified by column chromatography (methanol:chloroform=3:97)

Sources & evidence

ORD record
ord-be047e288f2448ae9583f8d353aba125
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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