m-Chloroperbenzoic acid → (3S)-tert-butyl 3-((6S)-6-((2-methyloxiran-2-yl)methyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate

HRID 884355Notes

Reaction equation

HRID 884355 reaction equation
[CH3:1][C:2](=[CH2:30])[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:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)[CH2:6][CH2:5]1.C1C=C(Cl)C=C(C(OO)=[O:39])C=1>ClCCl>[CH3:30][C:2]1([CH2:3][C@@:4]2([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:9][C:8](=[O:10])[N:7]([C@H:11]3[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:12]3)[CH2:6][CH2:5]2)[CH2:1][O:39]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58278658(S)-tert-butyl 3-((R)-6-(2-methylallyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate

Product 1

HCID 58278664(3S)-tert-butyl 3-((6S)-6-((2-methyloxiran-2-yl)methyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-tert-butyl 3-((R)-6-(2-methylallyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate (2.98 g, 7.2 mmol) in dichloromethane (200 mL) was added m-CPBA (77% maximum, 3.3 g, 2 equiv). The mixture was stirred 3 h at rt before being diluted by dichloromethane (150 mL), washed by 5% NaOH solution (2×40 mL), 30% aq sodium thiosulfate solution (30 mL), satd aq NaHCO3 (30 mL), 30% aq sodium thiosulfate solution (30 mL), satd aq NaHCO3 (30 mL), brine (30 mL), and dried over Na2SO4. Filtration and concentration gave crude (3S)-tert-butyl 3-((6S)-6-((2-methyloxiran-2-yl)methyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate (2.98 g 93% yield) which was used for next steps without further purification. LC-MS Method 1 tR=1.68 min., m/z 431 (M+1).

Workup

  1. washwashed by 5% NaOH solution (2×40 mL), 30% aq sodium thiosulfate solution (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-9ac8b0bd719648228d97be096f053ac0
Source dataset
uspto-grants-2012_08
Patent number
US08242111B2

Reaction notes

Loading…