HCID 59904930, compound → HCID 13150096, compound

HRID 2304553Notes

Reaction equation

HRID 2304553 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]1[C@@H:26]2[N:17]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C@H:25]2[OH:27])[CH2:16][CH2:15]1>CC(C)=O>[CH2:14]1[CH:26]2[N:17]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]2=[O:27])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 59904930HCID 59904930, compoundHCID 131709961Jones' reagent

Product 1

HCID 13150096HCID 13150096, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(Method B) Jones reagent (1.1 equiv., 1.77 mmol, 0.663 mL) was added to a solution of cis-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-10-ol (1.61 mmol, 304 mg, Example 35 below) in acetone (10 mL) in 5 minutes at room temperature (Szmuszkovicz, J.; Skaletzky, L. L. J. Org. Chem. 1967, 32, 3300). The mixture was concentrated in vacuo and H2O(15 mL) was added. The mixture was cooled with ice, basified with NaOH (10 mL, 1 N) and extracted with CH2Cl2 (3×20 mL). The combined extracts were washed with H2O(15 mL) and brine (15 mL), dried over Na2SO4 and concentrated in vacuo to give 1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-10-one as a yellow oil (198 mg). The 1H NMR spectrum was identical to that obtained by method (A).

Workup

  1. concentrationThe mixture was concentrated in vacuo and H2O(15 mL)
  2. additionwas added
  3. temperatureThe mixture was cooled with ice
  4. extractionextracted with CH2Cl2 (3×20 mL)
  5. washThe combined extracts were washed with H2O(15 mL) and brine (15 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a264561434674a0a8c73ff372497d6ef
Source dataset
uspto-grants-2002_08
Patent number
US06436954B1

Reaction notes

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