Water → HCID 23114348, compound

HRID 1787224Notes

Reaction equation

HRID 1787224 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:6]([C:8]1[C:16]2[O:15][CH2:14][CH:13]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[C:12]=2[C:11]([CH3:26])=[C:10]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:9]=1[CH3:35])=O.[BH4-].[Na+].O>CO.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH:23]([C:20]1[CH:21]=[CH:22][C:17]([CH:13]2[C:12]3[C:11]([CH3:26])=[C:10]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:9]([CH3:35])=[C:8]([CH2:6][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[C:16]=3[O:15][CH2:14]2)=[CH:18][CH:19]=1)([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 4311764Sodium borohydrideHCID 23114128N-(7-Formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide

Product 1

HCID 23114348HCID 23114348, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of pyrrolidine (0.20 mL, 2.4 mmol) in methanol (5 mL) was added titanium tetraisopropoxide (0.36 mL, 1.20 mmol) and N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (250 mg; 0.61 mmol) obtained in Example 20 at 0° C. and the resulting mixture was stirred at room temperature for 14 hours. To the reaction solution was added sodium borohydride (23.2 mg, 0.61 mol) at room temperature and the resulting mixture was stirred for 1.5 hours. Water was added to the reaction solution and the product was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 140 mg (yield: 49%) of the title compound. Amorphous substance.

Workup

  1. customobtained in Example 20 at 0° C.
  2. stirringthe resulting mixture was stirred for 1.5 hours
  3. concentrationthe product was concentrated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. customThe obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-336e57978599436d984e5142471ca859
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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