benzyl [(1S,2R)-2-hydroxy-1-methyl-2-pyridin-4-ylethyl]carbamate → 4-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)-

HRID 2093144Notes

Reaction equation

HRID 2093144 reaction equation
O[C@H](C1C=CN=CC=1)[C@@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4]>[OH-].[K+].CO.C1COCC1.O>[CH3:4][C@H:3]1[C@@H:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:7][C:6](=[O:15])[NH:5]1

Participants

4

Reactant 1

HCID 86630532benzyl [(1S,2R)-2-hydroxy-1-methyl-2-pyridin-4-ylethyl]carbamate

Product 1

HCID 8531614-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 86630533KOH MeOH THFSolvent

Procedure

A solution of benzyl [(1S,2R)-2-hydroxy-1-methyl-2-pyridin-4-ylethyl]carbamate in 7.5N aq. KOH/MeOH/THF (1:2:4, 7 mL) was stirred at room temperature overnight. The reaction was diluted with water (20 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford (4S,5R)-4-methyl-5-phenyl-1,3-oxazolidin-2-one. LCMS calc.=179.1; found=179.2 (M+1)+.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e50530411de4e3987a2137846b041d4
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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