(S)-tert-butyl 3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate → (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-piperidin-3-yl)-1,3-oxazinan-2-one

HRID 884357Notes

Reaction equation

HRID 884357 reaction equation
[OH:1][C:2]([CH3:31])([CH3:30])[CH2:3][C@@:4]1([C:24]2[CH:29]=[CH:28][CH:27]=[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>C(O)(C(F)(F)F)=O.C(Cl)Cl>[OH:1][C:2]([CH3:31])([CH3:30])[CH2:3][C@@:4]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=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

Participants

3

Reactant 1

HCID 58278660(S)-tert-butyl 3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate

Product 1

HCID 58278645(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-piperidin-3-yl)-1,3-oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(S)-tert-butyl 3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate (25 mg, 0.058 mmol) was dissolved in 20% TFA/CH2Cl2 (8 mL) solution and stirred 30 min at rt. The mixture was concentrated, redissolved in CH2Cl2 (25 mL), washed with satd aq NaHCO3 solution (10 mL), brine (8 mL), dried over Na2SO4. After filtration and concentration, the crude (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-piperidin-3-yl)-1,3-oxazinan-2-one as its TFA salt which was used without further purification. LC-MS Method 1 tR=0.86 min., m/z 333 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionredissolved in CH2Cl2 (25 mL)
  3. washwashed with satd aq NaHCO3 solution (10 mL), brine (8 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe crude (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-piperidin-3-yl)-1,3-oxazinan-2-one as its TFA salt which was used without further purification

Sources & evidence

ORD record
ord-948d07f8d68f4cb3aefb42ef4c1541a5
Source dataset
uspto-grants-2012_08
Patent number
US08242111B2

Reaction notes

Loading…