Sodium Bicarbonate → (R)-tert-butyl 1-(4-nitrophenyl)ethylcarbamate
Reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=1)([O-:4])=[O:3].[C:14](=[O:17])(O)[O-:15].[Na+]>C(Cl)Cl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]([NH:13][C:14](=[O:17])[O:15][C:8]([CH3:11])([CH3:9])[CH3:7])[CH3:12])=[CH:9][CH:10]=1)([O-:4])=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
(R)-1-(4-nitrophenyl)ethanamine hydrochloride salt (1.0 g, 4.9 mmol), tert-butoxycarbonyl (BOC) anhydride (1.18 g, 5.43 mmol), and 10.0 mL of 1M sodium bicarbonate solution were dissolved in DCM (15 mL) and allowed to stir at 25° C. for 24 h. The organic layer was collected, and the aqueous layer was washed with DCM. The combined organic layers were then washed with water and 0.1N HCl, dried over MgSO4, filtered, and concentrated to provide C1 as a white solid. Yield: 1.2 g, 92%. GC-MS=266. 1H NMR (500 MHz, d6-DMSO) δ: 8.15 (d, 2H), 7.56 (d, 1H), 7.52 (d, 2H), 4.68 (m, 1H), 1.32 (s, 9H), 1.27 (d, 3H).