Acetone → HCID 57949816, compound

HRID 2427719Notes

Reaction equation

HRID 2427719 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:8](=[O:16])[N:7]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=1)[CH2:6]2.[CH2:29]=O.[BH3-]C#N.[Na+].[O-]S([O-])(=O)=O.[Mg+2].[CH3:41][C:42]([CH3:44])=O>CO.C(Cl)(Cl)Cl.CO>[CH:42]([N:1]([CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:8](=[O:16])[N:7]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][C:25]([F:28])([F:26])[F:27])=[CH:22][CH:23]=1)[CH2:6]2)[CH3:29])([CH3:44])[CH3:41]

Participants

8

Reactant 5

HCID 180AcetoneHCID 712FormaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 86635673HCID 86635673, compound

Product 1

HCID 57949816HCID 57949816, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of 5-aminomethyl-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.040 g, 0.1 mmol), paraformaldehyde (0.025 g), acetone (0.5 mL), NaCNBH3 (0.013 g, 0.2 mmol), and anhydrous MgSO4 (0.050 g) in MeOH (6 mL) was stirred for 6 h. Workup and silica gel column chromatography using 10:1 CHCl3-MeOH afforded 5-[(isopropyl-methyl-amino)-methyl]-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.017 g, 39%). 1H NMR (300 MHz, CDCl3): δ ppm) 1.02 (d, 6H), 2.12 (s, 3H), 2.88 (q, 1H), 3.61 (s, 2H) 4.24 (s, 2H), 4.78 (s, 2H), 7.18 (d, 2H), 7.37 (d, 2H), 7.58 (s, 1H), 7.71 (s, 1H). GC-MS: m/z 445 (4-15)+, 367 (M−93)+.

Sources & evidence

ORD record
ord-2a702b22d515452588543c74c261061d
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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