1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 21224545, compound

HRID 1584257Notes

Reaction equation

HRID 1584257 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:13]([CH2:14]O)=[C:12]([CH3:16])[N:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:31]=[N+:32]=[N-:33])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>CN(C=O)C.C(Cl)Cl.CCOCC.C(OCC)(=O)C>[C:1]([O:5][C:6]([CH2:8][N:9]1[C:13]([CH2:14][N:31]=[N+:32]=[N-:33])=[C:12]([CH3:16])[N:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 21224552HCID 21224552, compound

Product 1

HCID 21224545HCID 21224545, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-t-butoxycarbonylmethyl-4-methyl-5-hydroxymethylimidazole (4.61 g, 20 mmol) in DMF (100 ml) was cooled to 0° C. and treated sequentially with diphenylphosphoryl azide (5.4 ml, 25 mmol) and DBU (3.7 ml, 25 ml). The resulting solution was allowed to warm gradually to room temperature and was then stirred there overnight. The DMF was rotavapped off, the residue dissolved in a minimum quantity of methylene chloride and the resulting solution diluted several fold with ether and ethyl acetate. This solution was washed sequentially with 1M citric acid, water, 10% sodium carbonate, brine and then dried over magnesium sulfate. Filtration and concentration gave an oil which was purified by flash chromatography (19:1 chloroform/methanol) to give the title compound as an oil: 1H NMR (CDCl3) d 1.48 (s, 9 H), 2.27 (s, 3 H), 4.28 (s, 2 H), 4.56 (s, 2 H), 7.43 (s, 1 H).

Workup

  1. washThis solution was washed sequentially with 1M citric acid, water, 10% sodium carbonate, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration
  4. customgave an oil which
  5. customwas purified by flash chromatography (19:1 chloroform/methanol)

Sources & evidence

ORD record
ord-667daf33450043cba5e3e2c289b184dc
Source dataset
uspto-grants-1999_08
Patent number
US05932606

Reaction notes

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