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

HRID 2275860Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]([CH3:21])([CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]#[N:10].O.[OH-].[Na+]>C1COCC1>[CH2:14]([O:13][CH2:12][CH2:11][C:8]([CH3:21])([NH2:7])[CH2:9][NH2:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under argon and at 0° C., 1.59 ml (1.59 mmol) of lithium aluminium hydride (1 N solution in diethyl ether) were added to 0.5 g (2.45 mmol) of 2-amino-4-(benzyloxy)-2-methylbutanonitrile Example 260A in 25 ml of dry THF. The reaction solution was stirred first at 0° C. for 30 min and then for another 1 h whilst slowly warming to room temperature. 245 μl of water, 245 μl of 2 N aqueous sodium hydroxide solution and 490 μl of water were then added carefully. The precipitate was filtered off and washed with THF and methanol, the filtrate was concentrated and the residue was purified by silica gel chromatography (mobile phase: dichloromethane/2 N ammonia in methanol=20/1, isocratic). This gave 0.30 g of the target compound (96% pure, 57% of theory).

Workup

temperaturefor another 1 h whilst slowly warming to room temperature
filtrationThe precipitate was filtered off
washwashed with THF and methanol
concentrationthe filtrate was concentrated
customthe residue was purified by silica gel chromatography (mobile phase: dichloromethane/2 N ammonia in methanol=20/1, isocratic)

Sources & evidence

ORD record: ord-cca3bdc92ee940e8822ba1fd2d0d0e7b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126998B2

Reaction notes

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