HCID 86729448, compound → ethyl 2-((4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-5-yl)oxy)acetate

HRID 1507031Notes

Reaction equation

HRID 1507031 reaction equation
[CH3:1][N:2]1[C:7](=O)[CH2:6][O:5][C:4]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:3]1=2>C1COCC1.CO>[CH3:1][N:2]1[CH2:7][CH2:6][O:5][C:4]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:3]1=2

Participants

4

Reactant 1

HCID 86729448HCID 86729448, compound

Product 1

HCID 86729447ethyl 2-((4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-5-yl)oxy)acetateYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
27 °C

Procedure

A solution of ethyl 2-((4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-5-yl)oxy)acetate (100 mg, 0.377 mmol) in anhydrous THF (3 mL) was cooled to 0° C. and BH3-Me2S (0.1 mL) added. The solution was stirred at 27° C. for 6 h, diluted with methanol and concentrated. The residue was partitioned between ethyl acetate (30 mL) and water (20 mL), the organic layer washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by preparative TLC. (72 mg, yield 76%) MS (ESI+) e/z: 252.2 [M+1]+. 1H NMR (CDCl3, 400 MHz), δ ppm: 6.87-6.76 (m, 1H), 6.62-6.52 (m, 1H), 6.40-6.28 (m, 1H), 4.70 (s, 2H), 4.34-4.22 (m, 2H), 4.18-4.06 (m, 2H), 3.21-3.07 (m, 2H), 2.99-2.85 (m, 3H), 1.33-1.25 (m, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate (30 mL) and water (20 mL)
  3. washthe organic layer washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-5de07be429844c5f9359638a41b93fc0
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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