Chloroform → HCID 58406144, compound

HRID 549103Notes

Reaction equation

HRID 549103 reaction equation
[CH3:1][C@@H:2]1[N:7]2[C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]=[C:10]([NH2:18])[C:9]=3[N:19]=[C:6]2[CH2:5][O:4][CH2:3]1.C(Cl)(Cl)Cl>FC(F)(F)C(O)=O.[Pt]=O>[CH3:1][C@@H:2]1[N:7]2[C:8]3[C:17]4[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=4[N:11]=[C:10]([NH2:18])[C:9]=3[N:19]=[C:6]2[CH2:5][O:4][CH2:3]1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 58406166HCID 58406166, compound

Product 1

HCID 58406144HCID 58406144, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

(11S)-11-Methyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (1.13 g, 4.45 mmol) was dissolved in 20 mL of trifluoroacetic acid and the solution was placed in a pressure bottle. Platinum oxide (1.34 g) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 2 days, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with 1,2-dichloroethane and the combined filtrates were concentrated under reduced pressure to give a peach colored oil. The oil was partitioned between dilute NH4OH solution and CH2Cl2. The layers were separated and the organic portion was washed successively with dilute NH4OH solution and brine. The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure to give a white foam. Chromatography (SiO2, 10-30% CMA/CHCl3) gave (11S)-11-methyl-2,3,4,8,10,11-hexahydro-1H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (0.57 g) as a white solid, mp 209-211° C.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with 1,2-dichloroethane
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. customto give a peach colored oil
  6. customThe oil was partitioned between dilute NH4OH solution and CH2Cl2
  7. customThe layers were separated
  8. washthe organic portion was washed successively with dilute NH4OH solution and brine
  9. dry with materialThe organic portion was then dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto give a white foam

Sources & evidence

ORD record
ord-a1cf8e79d5744c04b2c0404a95e6a96a
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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