Water → HCID 89545187, compound

HRID 509454Notes

Reaction equation

HRID 509454 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[C:19]3[CH2:20][CH2:21][CH2:22][C:23](=[O:24])[C:18]=3[O:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[BH4-].[Na+].O.C(OCC)(=O)C>C1COCC1.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[C:19]3[CH2:20][CH2:21][CH2:22][CH:23]([OH:24])[C:18]=3[O:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 895451743-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one

Product 1

HCID 89545187HCID 89545187, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To the 3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one (7.16 mg, 2.22 mmol) in THF/EtOH (v/v=1:1, 26 ml) at ° C., was added NaBH4 (101 mg, 1.66 mmol). The reaction mixture was stirred for 30 min before careful addition of water and extraction with ethyl acetate. The organic phase was washed with water and brine, dried over MgSO4 and concentrated to afford the title product which was used without further purification. 1H NMR (CDCl3) δ: 7.74 (s, 1H), 7.51 (s, 1H), 7.29-7.37 (m, 2H), 6.96 (s, 1H), 4.98 (br. s., 1H), 3.92 (s, 3H), 2.70-2.79 (m, 1H), 2.57-2.68 (m, 1H), 2.55 (br. s., 1H), 2.27-2.34 (m, 3H), 1.98-2.11 (m, 3H), 1.86-1.93 (m, 1H), 1.59 (s, 1H).

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-19f8ecb8134d47a08d1a31397a6486ad
Source dataset
uspto-grants-2015_08
Patent number
US09096582B2

Reaction notes

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