Water → rac-3-(Benzyloxy)-2-methylpropane-1,2-diamine

HRID 2275862Notes

Reaction equation

HRID 2275862 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]([CH3:20])([CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:9]#[N:10].O.[OH-].[Na+]>C1COCC1>[CH2:13]([O:12][CH2:11][C:8]([CH3:20])([NH2:7])[CH2:9][NH2:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 694771102-Amino-3-benzyloxy-2-methylpropionitrile

Product 1

HCID 90113971rac-3-(Benzyloxy)-2-methylpropane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon and at −78° C., 20.9 ml (20.9 mmol) of lithium aluminium hydride (1 N solution in diethyl ether) were added to 6.8 g (32.17 mmol, purity about 90%) of 2-amino-3-(benzyloxy)-2-methylpropionitrile Example 262A in 329 ml of dry THF. The reaction solution was at −78° C. for 1 h, at −20° C. for 2 h and at 0° C. for 2 h. 3.22 ml of water, 3.22 ml of 2 N aqueous sodium hydroxide solution and 6.44 ml of water were then added carefully. The precipitate was filtered off and washed with THF and methanol, and the filtrate was concentrated. This gave 8 g of the crude product. 7 g of this crude product were purified by silica gel chromatography (mobile phase: dichloromethane/2 N ammonia in methanol=from 20/1 to 10/1). This gave 1.52 g of the target compound (about 28% of theory).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with THF and methanol
  3. concentrationthe filtrate was concentrated
  4. custom7 g of this crude product were purified by silica gel chromatography (mobile phase: dichloromethane/2 N ammonia in methanol=from 20/1 to 10/1)

Sources & evidence

ORD record
ord-503e40909d834ccc85034df4e630229e
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

Loading…