Isopropanol → (4S,5S)-5-(4-tert-butylphenyl)-4-methyloxazolidin-2-one

HRID 10191Notes

Reaction equation

HRID 10191 reaction equation
C([O:8][C:9](=[O:25])[NH:10][C@@H:11]([CH3:24])[C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.CC(O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1.O>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([C@@H:12]2[O:25][C:9](=[O:8])[NH:10][C@H:11]2[CH3:24])=[CH:19][CH:18]=1)([CH3:21])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 69223528HCID 69223528, compound

Product 1

HCID 69222385(4S,5S)-5-(4-tert-butylphenyl)-4-methyloxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 9 g (26.5 mmole) [(S)-2-(4-tert-butylphenyl)-1-methyl-2-oxoethyl]-carbamic acid benzyl ester o in 40 mL toluene and 10 mL 2-propanol was added dropwise a solution of 0.7 g (18.42 mmole) sodium borohydride in 2 mL water containing 1 drop 50% sodium hydroxide. The reaction mixture was stirred at room temperature for 15 hrs. The layers were separated and the organic phase was washed with 25 mL 10% sodium hydroxide. 2-Propanol was removed under reduced pressure and the remaining toluene solution was heated under reflux for 1 hr. The solvent was removed under reduced pressure. The residue was recrystallized from diethyl ether/hexane to provide (4S,5S)-5-(4-tert-butylphenyl)-4-methyl-oxazolidin-2-one p, 3 g; m.p. 199–200° C.

Workup

  1. customThe layers were separated
  2. washthe organic phase was washed with 25 mL 10% sodium hydroxide
  3. custom2-Propanol was removed under reduced pressure
  4. temperaturethe remaining toluene solution was heated
  5. temperatureunder reflux for 1 hr
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was recrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-478d8c4c37604595a041594053e52ed2
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Reaction notes

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