Ethyl Acetate → 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butan-1-ol

HRID 1506403Notes

Reaction equation

HRID 1506403 reaction equation
[NH2:1][C:2]([CH3:38])([CH2:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:35](=[CH:36][CH:37]=1)[C:16]1=[N:17][O:18][C:19]([C:20]3[CH:21]=[N:22][N:23]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:24]=3[C:25]([F:28])([F:27])[F:26])=[C:15]1[CH2:14][CH2:13]2)[C:3](OCC)=[O:4].[BH4-].[Na+].C(OCC)(=O)C.[Cl-].[NH4+]>C(O)C.O>[NH2:1][C:2]([CH3:38])([CH2:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:35](=[CH:36][CH:37]=1)[C:16]1=[N:17][O:18][C:19]([C:20]3[CH:21]=[N:22][N:23]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:24]=3[C:25]([F:28])([F:27])[F:26])=[C:15]1[CH2:14][CH2:13]2)[CH2:3][OH:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67170053ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

Product 1

HCID 671710162-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butan-1-olYield 43.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (Preparation 50D, 80 mg, 0.153 mmol) in ethanol (1 mL) was added sodium borohydride (30 mg, 0.793 mmol) at room temperature. The reaction mixture was stirred at room temperature for 19 hr before ethyl acetate (4 mL) and water (2 ml) were added followed by the addition of saturated aqueous ammonium chloride solution (3 mL). The aqueous layer was separated and extracted with ethyl acetate (3×2 mL). The combined ethyl acetate solutions were dried over sodium sulfate and concentrated under reduced pressure to give a white solid. The solid was triturated with ethyl acetate to give 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butan-1-ol (32 mg, 0.066 mmol, 43.5% yield) as a white solid.

Workup

  1. additionwere added
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×2 mL)
  4. dry with materialThe combined ethyl acetate solutions were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a white solid
  7. customThe solid was triturated with ethyl acetate

Sources & evidence

ORD record
ord-73f227cf91e14b4e91f32643b5996ab3
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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