1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86695586, compound

HRID 1465720Notes

Reaction equation

HRID 1465720 reaction equation
CS(O[CH:6]1[CH2:12][C@@H:11]2[N:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:8]([CH2:9][CH2:10]2)[CH:7]1[C:21]([O:23][CH3:24])=[O:22])(=O)=O.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C@H:8]12[N:13]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@H:11]([CH2:10][CH2:9]1)[CH2:12][CH:6]=[C:7]2[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86695585HCID 86695585, compound

Product 1

HCID 86695586HCID 86695586, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1S,5R)-8-tert-butyl 2-methyl 3-(methylsulfonyloxy)-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (14.22 g, 39.15 mmol) and DBU (58.55 mL, 391.15 mmol) in DMF (73.87 mL) were heated at 100° C. for 10 hours. The reaction was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic fractions were combined, dried with sodium sulfate and concentrated to give crude product. The crude was purified using flash chromatography (0-100% Ethyl Acetate in Hexane) to give 5.45 g of (1S,5R)-8-tert-butyl 2-methyl 8-azabicyclo[3.2.1]oct-2-ene-2,8-dicarboxylate.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customto give crude product
  6. customThe crude was purified

Sources & evidence

ORD record
ord-3a2e125def8e4671a1c78a6d4203f649
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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