Water → 8-acetoxy-4-(2-(diphenylmethoxy)ethyl)-3,4-dihydro-2H-1,4-benzoxazine

HRID 2186727Notes

Reaction equation

HRID 2186727 reaction equation
[C:1]([O:4][C:5]1[C:14]2[O:13][CH2:12][C:11](=O)[N:10]([CH2:16][CH2:17][O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].B.C1COCC1.O>C1COCC1>[C:1]([O:4][C:5]1[C:14]2[O:13][CH2:12][CH2:11][N:10]([CH2:16][CH2:17][O:18][CH:19]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 224489238-acetoxy-4-(2-(diphenylmethoxy)ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 224489878-acetoxy-4-(2-(diphenylmethoxy)ethyl)-3,4-dihydro-2H-1,4-benzoxazineYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-acetoxy-4-(2-(diphenylmethoxy)ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzooxazine (630 mg) was dissolved in THF (10 ml), and a 1.0M borane THF solution (4.5 ml) was added to the resultant solution at 0° C., followed by stirring at room temperature for 4 hours. After water was added to the reaction solution to terminate reaction, the reaction solution was extracted with ethyl acetate. The resultant organic layer was washed with water, saturated sodium bicarbonate water, water and saturated brine, dried over sodium sulfate, and then concentrated. The residue was purified by medium-pressure column chromatography (solvent:ethyl acetate/cyclohexane=1/5) to obtain the colorless oily object compound (550 mg, yield 90%).

Workup

  1. customto terminate
  2. customreaction
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe resultant organic layer was washed with water, saturated sodium bicarbonate water, water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by medium-pressure column chromatography (solvent:ethyl acetate/cyclohexane=1/5)

Sources & evidence

ORD record
ord-f7afe46f86564b3eaf7eeeec569cdb24
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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