Sodium Hydroxide → HCID 86616086, compound

HRID 2353983Notes

Reaction equation

HRID 2353983 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:16][CH2:15][CH2:14][C:13](=O)[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]2=3)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[F:23][C:24]([F:38])([F:37])[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:28][NH2:29].[BH4-].[Na+].[OH-].[Na+]>COCCOCCOC.CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:23][C:24]([F:37])([F:38])[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:32]=1)[CH2:28][NH:29][CH:13]1[CH2:14][CH2:15][CH2:16][N:10]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:22])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[C:11]2[CH:21]=[CH:20][CH:19]=[CH:18][C:12]1=2

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 2668521-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-oneHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 4311764Sodium borohydride

Product 1

HCID 86616086HCID 86616086, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 8150DiglymeSolvent

Procedure

A mixture of (+/−)1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-benzo[b]azepin-5-one (500 mg, 1.58 mmol), 3,5-Bis(trifluoromethyl)benzylamine (423 mg, 1.74 mmol) and titanium(IV) isopropoxide (0.59 ml, 1.97 mmol) in diglyme (2 ml) is stirred at room temperature for 22 hours. The mixture is diluted with methanol (7 ml) and treated with sodium borohydride (90 mg, 2.37 mmol), then stirred at room temperature for 6 hours. The mixture is treated with 0.1N aqueous NaOH (15 ml) and stirred for 10 minutes, then filtered. The filter cake is washed with 1:1 ethanol:diethyl ether. The filtrate is diluted with water (70 ml) and extracted with ethyl acetate (2×30 ml). The combined organic extracts are washed with brine, dried (Na2SO4) and concentrated to an oil. The oil is purified by silica gel column chromatography (eluent, 15% ethyl acetate in hexanes) to give the title compound as a solid. Mass spectrum (ES+): 543 (M+H).

Workup

  1. stirringstirred at room temperature for 6 hours
  2. stirringstirred for 10 minutes
  3. filtrationfiltered
  4. washThe filter cake is washed with 1:1 ethanol
  5. additionThe filtrate is diluted with water (70 ml)
  6. extractionextracted with ethyl acetate (2×30 ml)
  7. washThe combined organic extracts are washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to an oil
  10. customThe oil is purified by silica gel column chromatography (eluent, 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e24b9e76f1dc44c0abe341301141a8e3
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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