Thionyl Chloride → 1,2,3,3a,8,8a-Hexahydroindeno[1,2-c]pyrrole

HRID 1020316Notes

Reaction equation

HRID 1020316 reaction equation
[C:1]1(=O)[CH:5]2[CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[CH:4]2[CH2:3][NH:2]1.S(Cl)(Cl)=O.C1(=NO)C2CC3C=CC=CC=3C2C1>O1CCOCC1>[CH2:1]1[NH:2][CH2:3][CH:4]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH2:6][CH:5]12

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 3729139HCID 3729139, compoundHCID 58598870HCID 58598870, compound

Product 1

HCID 115791751,2,3,3a,8,8a-Hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,3a,8,8a-Tetrahydro-2H-2-aza-cyclopenta[a]inden-1-one. Thionyl chloride (1.9 mL, 26.4 mmol) was added to a solution of 2,2a,7,7a-tetrahydro-cyclobuta[a]inden-1-one oxime (1.5 g, 8.8 mmol) in 1,4-dioxane (44 mL), and stirred overnight at room temperature. The reaction was quenched with saturated aqueous NaHCO3 (100 mL), and extracted with EtOAc (3×50 mL). The organic extracts were washed with brine, dried over MgSO4, and concentrated to give the subtitle compound and its regioisomer, which were used without further purification. MS calculated for C11H11NO+H: 174, observed: 174.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 (100 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-08b1a34f7bbf489887d412cffbcddfa8
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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