Tetrabutylammonium Fluoride → 2-[(11R)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol

HRID 1035508Notes

Reaction equation

HRID 1035508 reaction equation
[Si]([O:8][C:9]([C@@H:12]1[N:17]2[C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=[CH:20][C:19]=3[N:28]=[C:16]2[CH2:15][O:14][CH2:13]1)([CH3:11])[CH3:10])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[C:18]1[N:17]3[C@@H:12]([C:9]([OH:8])([CH3:10])[CH3:11])[CH2:13][O:14][CH2:15][C:16]3=[N:28][C:19]=1[CH:20]=[N:21]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67156212(11R)-11-(1-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline

Product 1

HCID 671569042-[(11R)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-olYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

(11R)-11-(1-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (1.14 g, 2.91 mmol) was dissolved in 30 mL of THF and the stirred solution was cooled to −50° C. Tetrabutylammonium fluoride (1.0 M solution in THF, 4.37 mL) was added slowly and the stirred reaction mixture was allowed top warm to ambient temperature over 4 hours. The reaction mixture was concentrated under reduced pressure and the resulting material was partitioned between 50 mL of CH2Cl2 and saturated NaHCO3 solution. The layers were separated and the organic portion was washed with brine (4×20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 8% MeOH/CHCl3) gave 2-[(11R)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol (755 mg) as an off-white solid.

Workup

  1. customthe stirred reaction mixture
  2. temperaturewas allowed top warm to ambient temperature over 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe resulting material was partitioned between 50 mL of CH2Cl2 and saturated NaHCO3 solution
  5. customThe layers were separated
  6. washthe organic portion was washed with brine (4×20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74e7f06de19c4e189a6957c4d9cfc2b9
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

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