Methanol → (11S)-11-hydroxymethyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline

HRID 549169Notes

Reaction equation

HRID 549169 reaction equation
C([O:8][CH2:9][C@@H:10]1[N:15]2[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[CH:18][C:17]=3[N:26]=[C:14]2[CH2:13][O:12][CH2:11]1)C1C=CC=CC=1.CO.C(Cl)(=O)C>[Pd].C(Cl)(Cl)Cl>[OH:8][CH2:9][C@@H:10]1[N:15]2[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[CH:18][C:17]=3[N:26]=[C:14]2[CH2:13][O:12][CH2:11]1

Participants

6

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 67157259(11S)-11-[(benzyloxy)methyl]-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline

Product 1

HCID 67156623(11S)-11-hydroxymethyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolineYield 35.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent

Procedure

(11S)-11-[(benzyloxy)methyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (7.5 g, 22 mmol) was added to a mixture of methanol (270 mL) and acetyl chloride (3.0 mL, 43 mmol) in a pressure bottle. Palladium on carbon (10%, 1.5 g) was then added and the reaction mixture was shaken under H2 at 48 PSI (3.3×105 Pa). After 11 days, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with methanol. The combined filtrates were treated with 2 mL of 50% aqueous NaOH solution and the mixture was concentrated under reduced pressure to afford an orange oil. Chromatography (SiO2, 0-30% CMA/CHCl3) gave an oil that was concentrated from acetonitrile under reduced pressure to give 2.0 g of (11S)-11-hydroxymethyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline as a tan solid.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with methanol
  4. additionThe combined filtrates were treated with 2 mL of 50% aqueous NaOH solution
  5. concentrationthe mixture was concentrated under reduced pressure
  6. customto afford an orange oil
  7. concentrationwas concentrated from acetonitrile under reduced pressure

Sources & evidence

ORD record
ord-48056b042b084e4eabb04610f937ccb1
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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