Trifluoroacetic acid → HCID 58109296, compound

HRID 2037586Notes

Reaction equation

HRID 2037586 reaction equation
[CH2:1]([C@@:4]1([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]2[CH2:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([C@@:4]1([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58109445HCID 58109445, compound

Product 1

HCID 58109296HCID 58109296, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)piperidine-1-carboxylate (700 mg, 1.67 mmol) in CH2Cl2 (16 mL) was added TFA (3.2 mL) at 0° C. The mixture was stirred at rt for 2 h. Then aqueous solution of NaHCO3 was added, and the mixture was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by preparative TLC to give (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-piperidin-3-yl)-1,3-oxazinan-2-one (530 mg, 100%).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-c422c0ace4244fe3aaba9be25f1585af
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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