1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10221000, compound

HRID 594950Notes

Reaction equation

HRID 594950 reaction equation
N12CCCN=C1CCCCC2.CS(O[CH:17]1[CH2:23][CH:22]2[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:19]([CH2:20][CH2:21]2)[CH:18]1[C:32]([O:34][CH3:35])=[O:33])(=O)=O>CN(C=O)C>[CH:19]12[N:24]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH:22]([CH2:21][CH2:20]1)[CH2:23][CH:17]=[C:18]2[C:32]([O:34][CH3:35])=[O:33]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86689214HCID 86689214, compound

Product 1

HCID 10221000HCID 10221000, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (8.05 g, 53 mmol) was added into a solution of 8-tert-butyl 2-methyl 3-(methylsulfonyloxy)-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (5.29 mmol) in DMF at room temperature and the reaction solution was heated at 100° C. for 16 h. The resulting solution was concentrated and purified using flash chromatography (0-60% ethyl acetate in hexane) to give the titled compound (905 mg, yield 64% for three steps).

Workup

  1. concentrationThe resulting solution was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-32d5db2bf0074c09bce0ee146c81c7d4
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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