Carbonocyanidic acid, methyl ester → HCID 9838701, compound

HRID 594948Notes

Reaction equation

HRID 594948 reaction equation
[O:1]=[C:2]1[CH2:8][CH:7]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.C([N-]C(C)C)(C)C.[Li+].C([C:27]([O:29][CH3:30])=[O:28])#N>O1CCCC1>[O:1]=[C:2]1[CH2:3][CH:4]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:7]([CH2:6][CH2:5]2)[CH:8]1[C:27]([O:29][CH3:30])=[O:28]

Participants

5

Reactant 3

HCID 28660Carbonocyanidic acid, methyl esterHCID 2724682Lithium diisopropylamideHCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate

Product 1

HCID 9838701HCID 9838701, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (55.5 mL) was added to a flask containing tert-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (10 g, 0.0444 mol). At −78° C., lithium diisopropylamide (24.4 mL, 0.0488 mol) was added dropwise to the reaction. The reaction was allowed to stir for 1 hr, then methyl cyanoformate (4.226 mL, 0.05326 mol) was added dropwise at −78° C. The reaction was let to stir for 5 hrs at room temperature. The reaction was quenched using saturated ammonium chloride solution. Some of the tetrahydrofuran was removed in vacuo. The remaining THF and ammonium chloride mixture was extracted using ethyl acetate three times. The combined ethyl acetate layers were washed with water and dried over sodium sulfate. The solution was filtered, was concentrated, and was purified using flash chromatography (0-100% ethyl acetate in hexane). A yellow oil was recovered (88% yield).

Workup

  1. stirringto stir for 5 hrs at room temperature
  2. customThe reaction was quenched
  3. customSome of the tetrahydrofuran was removed in vacuo
  4. extractionThe remaining THF and ammonium chloride mixture was extracted
  5. washThe combined ethyl acetate layers were washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationwas concentrated
  9. customwas purified
  10. customA yellow oil was recovered (88% yield)

Sources & evidence

ORD record
ord-6c0d045b0c0b42349a4c3d7f47f8cc5a
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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