Sodium borohydride → (9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)methanol

HRID 1506429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506429
[O:1]1[CH2:6][CH2:5][N:4]([C:7]23[C:34]4[CH:33]=[CH:32][C:31]([CH:35]=[O:36])=[CH:30][C:29]=4[O:28][CH2:27][CH:8]2[C:9]([C:12]2[O:16][N:15]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:13]=2[C:23]([F:26])([F:25])[F:24])=[N:10][O:11]3)[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[O:1]1[CH2:2][CH2:3][N:4]([C:7]23[C:34]4[CH:33]=[CH:32][C:31]([CH2:35][OH:36])=[CH:30][C:29]=4[O:28][CH2:27][CH:8]2[C:9]([C:12]2[O:16][N:15]=[C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:13]=2[C:23]([F:25])([F:26])[F:24])=[N:10][O:11]3)[CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 866699039b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazole-7-carbaldehyde

Produkt 1

HCID 67169503(9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazole-7-carbaldehyde (Preparation 60F, 0.070 g, 0.140 mmol) in methanol (1.0 mL) at room temperature was added sodium borohydride (1.43 mg, 0.038 mmol). The reaction mixture was stirred at room temperature for 30 min. Methanol was removed under reduce pressure, and the residue was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded (9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)methanol as a yellow oil. The product had an HPLC ret. time=2.83 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=502.0.

Aufarbeitung

  1. customMethanol was removed
  2. additionthe residue was diluted with dichloromethane
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-09a3e38745e749c9a34975d6aefad4ce
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216972B2

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