Water → rac-4-(Benzyloxy)-2-methylbutane-1,2-diamine

Temperature

0 °C

0.5 g (2.45 mmol) of rac-2-amino-4-(benzyloxy)-2-methylbutanonitrile from Example 32A in 25 ml of dry THF were admixed under argon at 0° C. with 1.59 ml (1.59 mmol) of lithium aluminium hydride (1 N solution in diethyl ether). The reaction solution was first stirred at 0° C. for 30 min and then stirred for 1 h, gradually coming to room temperature. Then 245 μl of water, 245 μl of 2 N aqueous sodium hydroxide solution and 490 μl of water were added cautiously. The precipitate was filtered off and washed with THF and methanol, the filtrate was concentrated and the residue was purified by means of silica gel chromatography (eluent:dichloromethane/2 N ammonia in methanol=20/1, isocratic). 0.30 g of the target compound (96% purity, 57% of theory) was obtained.

1. stirringstirred for 1 h
2. customgradually coming to room temperature
3. filtrationThe precipitate was filtered off
4. washwashed with THF and methanol
5. concentrationthe filtrate was concentrated
6. customthe residue was purified by means of silica gel chromatography (eluent:dichloromethane/2 N ammonia in methanol=20/1, isocratic)

ORD record

ord-1cf4e6d3016c48b88a4c8cd9f39b4812

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422285B2