Ethanol → HCID 67170078, compound

HRID 1506536Notes

Reaction equation

HRID 1506536 reaction equation
[NH2:1][C:2]1([C:35](OC)=[O:36])[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]3[C:32](=[CH:33][CH:34]=2)[C:13]2=[N:14][O:15][C:16]([C:17]4[C:21]([C:22]([F:25])([F:24])[F:23])=[C:20]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[O:19][N:18]=4)=[C:12]2[CH2:11][CH2:10]3)[CH2:3]1.CCO.[BH4-].[Na+].[OH-].[Na+]>O.ClCCl>[NH2:1][C:2]1([CH2:35][OH:36])[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]3[C:32](=[CH:33][CH:34]=2)[C:13]2=[N:14][O:15][C:16]([C:17]4[C:21]([C:22]([F:25])([F:24])[F:23])=[C:20]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)[O:19][N:18]=4)=[C:12]2[CH2:11][CH2:10]3)[CH2:3]1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 67169476HCID 67169476, compound

Product 1

HCID 67170078HCID 67170078, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 1-amino-3-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)cyclopentanecarboxylate (Preparation 121F, 160 mg, 0.306 mmol) was mixed with EtOH (2 mL), dichloromethane (1 mL) and sodium borohydride (57.8 mg, 1.528 mmol). The mixture was stirred at room temperature overnight. Next, 2N aqueous sodium hydroxide solution (5 mL) was added. The mixture was stirred at 40° C. for 30 min. and cooled. Water (10 mL) was added. The mixture was extracted with EtOAc (10 mL, 2×5 mL). The combined ethyl acetate extracts were dried (sodium sulfate) and concentrated under reduced pressure to give a (1-amino-3-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)cyclopentyl)methanol (151 mg, 0.305 mmol, 100% yield) as a foam solid.

Workup

  1. stirringThe mixture was stirred at 40° C. for 30 min.
  2. temperaturecooled
  3. extractionThe mixture was extracted with EtOAc (10 mL, 2×5 mL)
  4. dry with materialThe combined ethyl acetate extracts were dried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-181b0c1f1cc8444bbe91db2fe92333ef
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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