Boron tribromide → (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

HRID 1036381

Reaction equation

HRID 1036381 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@:13]1([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[CH:7]=[CH:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@:13]1([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67414221(R)-4-(6-Methoxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-4-(6-Methoxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (215 mg, 0.836 mmol) was dissolved in methylene chloride (5.4 mL) and, at −78° C., 2.5 mL of 1.0 M boron tribromide in methylene chloride was added and was stirred under N2 to rt. After 5 h, TLC and LCMS showed no starting material (1.34, 213.92, 100%) but only product (1.02, 200.02, 100%). The reaction was quenched with water (10 mL) and extracted with ether (100 mL) and EtOAc (3×10 mL). The organic layer was washed with brine and dried over Na2SO4. After concentration, a white solid was obtained (200 mg, 99%).

Workup

  1. customThe reaction was quenched with water (10 mL)
  2. extractionextracted with ether (100 mL) and EtOAc (3×10 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customa white solid was obtained (200 mg, 99%)

Sources & evidence

ORD record
ord-09c50dd259114e4393e101208399b93d
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Linked notes

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