(-)-Pseudoephedrine → (4R,5R)-2-(2-Bromo-4-fluoro-phenyl)-3,4-dimethyl-5-phenyl-oxazolidine

HRID 1397191Notes

Reaction equation

HRID 1397191 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][C@@H:12]([NH:21][CH3:22])[C@H:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]1[N:21]([CH3:22])[C@H:12]([CH3:11])[C@@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:5]1

Participants

4

Reactant 2

HCID 62946(-)-PseudoephedrineHCID 27733192-Bromo-4-fluorobenzaldehyde

Product 1

HCID 66632944(4R,5R)-2-(2-Bromo-4-fluoro-phenyl)-3,4-dimethyl-5-phenyl-oxazolidineYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution 2-bromo-4-fluorobenzaldehyde (15.2 g, 74.9 mmol) in toluene (80 ml) was added (1R,2R)-(−)-pseudoephedrine (13.6 g, 82 mmol) and the resulting mixture was refluxed removing water using a Dean-Stark trap for 16 h. The reaction was halted and cooled down to room temperature. The solution was washed with citric acid solution (1M, 100 ml), saturated sodium bicarbonate solution (50 ml), brine (50 ml) and dried (MgSO4). Then, it was filtered and the solvent was evaporated under vacuum to give title compound as yellow oil. (26.2, yield=97%).

Workup

  1. temperaturethe resulting mixture was refluxed
  2. customremoving water using a Dean-Stark trap for 16 h
  3. washThe solution was washed with citric acid solution (1M, 100 ml), saturated sodium bicarbonate solution (50 ml), brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationThen, it was filtered
  6. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-34e537fad1ed47aab22195ffbbbde410
Source dataset
uspto-grants-2014_12
Patent number
US08901159B2

Reaction notes

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