Ethyl Acetate → tert-Butyl-(4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-methylthiophenyl)-1,3-oxazolidine-3-carboxylate

HRID 2234754Notes

Reaction equation

HRID 2234754 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:12][C:11]([CH3:14])([CH3:13])[N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:9]2[CH2:22][F:23])=[CH:4][CH:3]=1.[CH3:24][S:25]SC.[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1>[C:18]([O:17][C:15]([N:10]1[C@H:9]([CH2:22][F:23])[C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([S:25][CH3:24])=[CH:3][CH:4]=2)[O:12][C:11]1([CH3:14])[CH3:13])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12232Dimethyl DisulfideHCID 25517Ammonium ChlorideHCID 58631058tert-butyl (4S,5R)-5-(4-bromophenyl)-4-(fluoromethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 68718131tert-Butyl-(4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-methylthiophenyl)-1,3-oxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-butyl lithium (n-BuLi), (1.78 g, 28 mmol, 1.2 eq) was added to a solution of tert-butyl (4S,5R)-5-(4-bromophenyl)-4-(fluoromethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (9.0 g, 23 mmol) in 30 ml of anhydrous tetrahydrofuran (THF) at −78° C. in 30 min, and the reaction mixture was stirred for 30 minutes under N2. 3.1 ml of dimethyldisulfide (1.5 eq) was added, and stirred for 30 min. The reaction mixture was warmed up to room temperature and stirred for 1 hour. A saturated solution of ammonium chloride (50 ml) and ethyl acetate (50 ml) was added and stirred for 30 min. The organic layer was washed with brine (50 ml) and dried over sodium sulfate. After purification, via a column, 8.15 g of white solid of the desired product was obtained.

Workup

  1. stirringstirred for 30 min
  2. stirringstirred for 1 hour
  3. stirringstirred for 30 min
  4. washThe organic layer was washed with brine (50 ml)
  5. dry with materialdried over sodium sulfate
  6. customAfter purification

Sources & evidence

ORD record
ord-826395f10975438791cff1657c7382e9
Source dataset
uspto-grants-2010_05
Patent number
US07713950B2

Reaction notes

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