Water → HCID 69073065, compound

HRID 553951Notes

Reaction equation

HRID 553951 reaction equation
C([SiH](CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]2[CH2:32][O:31][C@@H:30](O)[CH:29]3[CH2:34][CH2:35][CH2:36][C:37](=[O:38])[N:28]23)=[CH:23][CH:22]=1.O>ClCCl.C(OCC)(=O)C>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C@@H:27]2[CH2:32][O:31][CH:30]=[C:29]3[CH2:34][CH2:35][CH2:36][C:37](=[O:38])[N:28]23)=[CH:25][CH:26]=1.[F:20][C:21]1[CH:22]=[CH:23][C:24]([C@@H:27]2[CH2:32][O:31][CH2:30][C@H:29]3[CH2:34][CH2:35][CH2:36][C:37](=[O:38])[N:28]23)=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 962WaterHCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 69072724HCID 69072724, compound

Product 2

HCID 69073065HCID 69073065, compoundHCID 69076531HCID 69076531, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Triethylsilane (5.5 mL) and trimethylsilyl trifluoromethanesulfonate (442 μL) were added to a solution of (R*)-4-(4-fluorophenyl)-1-hydroxyhexahydropyrido[2,1-c][1,4]oxazin-6-one (324 mg) in dichloromethane (10 mL), and the reaction solution was reacted at room temperature for 1.5 hours. Then, the reaction solution was heated to 60° C. and stirred for two hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 69.2 mg of (R*)-4-(4-fluorophenyl)-3,4,8,9-tetrahydro-7H-pyrido[2,1-c][1,4]oxazin-6-one and 52.8 mg of (4R*,9aR*)-4-(4-fluorophenyl)hexahydropyrido[2,1-c][1,4]oxazin-6-one. The physical properties of (R*)-4-(4-fluorophenyl)-3,4,8,9-tetrahydro-7H-pyrido[2,1-c][1,4]oxazin-6-one are as follows.

Workup

  1. customthe reaction solution was reacted at room temperature for 1.5 hours
  2. customthe organic layer was separated
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-9f2dbedc8b7047b5b0f3284e3b34281f
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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