Methylamine → 3-(tert-Butyldimethylsiloxymethyl)benzylamine

Methylamine (a 30% ethanol solution, 400 mL) was added to a solution of 3-(tert-butyldimethylsiloxymethyl)benzylphthalimide (11.93 g, 31.3 mmol) in ethanol (200 mL) at room temperature, and the resulting mixture was stirred at room temperature for 5 minutes and then at 90° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with diethyl ether and stirred at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure at 20° C. and the residue was diluted with diethyl ether (300 mL), and ultrasonic waves were applied thereto for 1 hour. The resulting cloudy liquid was filtered and the filtrate was concentrated under reduced pressure at 20° C. to obtain the title compound (6.23 g, 79%) as a white solid.

1. waitat 90° C. for 3 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionthe residue was diluted with diethyl ether
4. stirringstirred at room temperature for 30 minutes
5. concentrationThe reaction solution was concentrated under reduced pressure at 20° C.
6. additionthe residue was diluted with diethyl ether (300 mL), and ultrasonic waves
7. waitfor 1 hour
8. filtrationThe resulting cloudy liquid was filtered
9. concentrationthe filtrate was concentrated under reduced pressure at 20° C.

ORD record

ord-5098ddcf13a74b65b237e7311e8fa6e2

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06787560B2