Water → HCID 91507228, compound

HRID 1393357Notes

Reaction equation

HRID 1393357 reaction equation
[BH4-].[Na+].[C:3]1([CH:9]2[C:14](=O)[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[C:19]([C:20](O)=[O:21])[C:11]=3[O:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:3]1([CH:9]2[CH:14]=[N:13][C:12]3[CH:16]=[CH:17][CH:18]=[C:19]([CH2:20][OH:21])[C:11]=3[O:10]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 23033881HCID 23033881, compound

Product 1

HCID 91507228HCID 91507228, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Boron trifluoride ether complex (1.83 ml, 14.86 mmol) was added dropwise to a suspension of sodium borohydride (422 mg, 11.14 mmol) in tetrahydrofuran (30 ml) with stirring under ice cooling in 10 min. To this reaction mixture was added a solution of (±)-2-phenyl-1,4-benzoxazin-3-one-8-carboxylic acid (500 mg, 1.86 mmol) in tetrahydrofuran (6 ml) and the mixture was stirred at the same temperature for 5 min. and then at room temperature for 1.5 hrs. The reaction mixture was cooled with ice and water (20 ml) was added dropwise thereto. The mixture was neutralized with saturated sodium bicarbonate solution and then extracted with ethyl acetate. The extract was washed with water and brine in turn and dried. The solvent was distilled off under reduced pressure to give (±)-2-phenyl-1,4-benzoxazine-8-methanol (397 mg, 89%) as a pale orange oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 5 min.
  2. waitat room temperature for 1.5 hrs
  3. additionwas added dropwise
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and brine in turn
  6. customdried
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1ea6e7d25c954d3a9aff7da0308ede78
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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