Aminoacetaldehyde dimethyl acetal → N-(3,5-difluoro-4-methoxybenzyl)-aminoacetaldehyde dimethyl acetal

HRID 981573Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[O:10][CH3:11])[CH:5]=O.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH2:17].[BH4-].[Na+]>C(O)C>[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH:17][CH2:5][C:4]1[CH:3]=[C:2]([F:1])[C:9]([O:10][CH3:11])=[C:8]([F:12])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3,5-Difluoro-4-methoxybenzaldehyde (3.38 g, 0.0196 mole) was added to aminoacetaldehyde dimethyl acetal (2.14 ml, 0.0196 mole) and the mixture was heated at 100° C. for 2 hours. The reaction mixture was cooled in ice, diluted with ethyl alcohol (35 ml), and sodium borohydride (0.743 g., 0.0196 mole) was added and the mixture was stirred overnight at 25° C. The solvent was removed under reduced pressure, the residue was dissolved in ethyl acetate, and the solution was washed with water and brine and then dried with sodium sulfate. The mixture was filtered, and the solvent removed under reduced pressure to give N-(3,5-difluoro-4-methoxybenzyl)-aminoacetaldehyde dimethyl acetal as an oil (4.94 g, 96%).

Workup

temperatureThe reaction mixture was cooled in ice
additionwas added
customThe solvent was removed under reduced pressure
dissolutionthe residue was dissolved in ethyl acetate
washthe solution was washed with water and brine
dry with materialdried with sodium sulfate
filtrationThe mixture was filtered
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-a8a08d2d6cc84142aa32ff5792554b9f
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04992459

Reaction notes

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