Sodium Hydroxide → 1-Tert-butoxycarbonyl-2-methylpropyleneimine
Reaction equation
C1(C)C=CC(S(OCC([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O)(C)C)(=O)=O)=CC=1.[OH-].[Na+]>CCOCC>[C:19]([O:18][C:16](=[NH:15])[CH:20]=[C:19]([CH3:22])[CH3:21])([CH3:20])([CH3:21])[CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred mixture of 2-tert-butoxycarbonylamino-2-methyl-1-propyl p-toluenesulfonate (8.2 g, 23.88 mmol) and powdered NaOH (6.7 g, 0.151 mol) in Et2O (200 mL) was heated under reflux for 10 hr. After cooling, the mixture was filtered. And the filtrate was washed with water, brine, dried over Na2SO4, and evaporated. The residue was chromatographed on silica-gel with n-hexane:EtOAc (6:1 v/v) as eluent to give 2.7 g (66.2%) 1-tert-butoxycarbonyl-2-methylpropylene imine as an oil. 1H-NMR (CDCl3) δ 1.29 (s, 61H), 1.47 (s, 9H), 2.05 (s, 2H).