1,8-Diazabicyclo(5.4.0)undec-7-ene → 1,2-Dihydro-1-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 1068775Notes

Reaction equation

HRID 1068775 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=O)=O.[NH:20]1[C:28]2[N:23]3[C:24](=[N:29][CH:30]=[C:22]3[C:21]1=[O:31])[CH:25]=[CH:26][CH:27]=2.C1CCN2C(=NCCC2)CC1>CN(C=O)C.O>[C:16]([O:15][C:13]([N:10]1[CH2:11][CH2:12][CH:7]([CH2:6][N:20]2[C:28]3[N:23]4[C:24](=[N:29][CH:30]=[C:22]4[C:21]2=[O:31])[CH:25]=[CH:26][CH:27]=3)[CH2:8][CH2:9]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylateHCID 117449051,2-Dihydro-1,4,7b-triazacyclopent[cd]inden-2-one

Product 1

HCID 211901151,2-Dihydro-1-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-1,4,7b-triazacyclopent[cd]inden-2-oneYield 43.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture containing 5.68 g (20.0 mM) of (1-tert-butoxycarbonylpiperidin-4-ylmethyl) methanesulfonate, 4.35 g (20.0 mM) of 1,2-dihydro-1,4,7b-triazacyclopent[cd]inden-2-one.2NaCl, and 3.58 ml (24.0 mM) of DBU in 50 ml of DMF was heated at 80° C. for 2 hours. After completion of the reaction, the reaction mixture was poured in 50 ml of iced water and extracted with 100 ml of ethyl acetate. The organic layer was washed with 50 ml of purified water twice and, then, with 50 ml of saturated aqueous NaCl solution and dried over Na2SO4. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate-ethanol=10:1) to provide 3.00 g (yield 42.1%) of the title compound as a brown amorphous substance.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with 100 ml of ethyl acetate
  3. washThe organic layer was washed with 50 ml of purified water twice
  4. dry with materialwith 50 ml of saturated aqueous NaCl solution and dried over Na2SO4
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate-ethanol=10:1)

Sources & evidence

ORD record
ord-a64ba7d79c854b4fa94b4744f47d8359
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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