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 1506429노트

반응식

HRID 1506429 반응식
[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

참가 물질

4

반응물 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

생성물 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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-09a3e38745e749c9a34975d6aefad4ce
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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