Acetophenone → HCID 11698174, compound

HRID 2427718Notes

Reaction equation

HRID 2427718 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[C:8](=[O:13])[N:7]([C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:6]2.[C:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=O)[CH3:28].[BH3-]C#N.[Na+].C(Cl)(Cl)Cl.CO>CCO>[CH3:12][C:10]1[CH:11]=[C:3]([CH2:2][NH:1][CH:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:28])[CH:4]=[C:5]2[C:9]=1[C:8](=[O:13])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:6]2

Participants

6

Reactant 4

HCID 7410AcetophenoneHCID 5003444Sodium cyanoborohydrideHCID 21584188Chloroform methanolHCID 67252415HCID 67252415, compound

Product 1

HCID 11698174HCID 11698174, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-aminomethyl-7-methyl-2-(4-trifluoromethoxybenzoyl)-2,3-dihydro-isoindol-1-one (0.053 g, 0.15 mmol), acetophenone (0.036 g, 0.30 mmol), Ti(i-OPr)4 (1 mL), and NaBH3CN (0.1 g, 1.6 mmol) in EtOH (2 mL) was stirred for 6 h. Workup and silica gel column chromatography using 10:1 CHCl3-MeOH afforded 7-methyl-5-[(1-phenyl-ethylamino)-methyl]-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.030 g, 44%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.38 (d, 3H), 1.64 (bs, 1H), 2.73 (s, 3H), 3.62 (dd, 2H), 3.82 (q, 1H), 4.21 (s, 2H), 4.75 (s, 2H), 7.08-7.39 (m, 11H). GC-MS: m/z 439 (M-15)+.

Sources & evidence

ORD record
ord-1341fb9448564c0ea6d93518906cde0f
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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