tert-butyl 1-(4-chlorophenyl)-2-hydroxyethylcarbaMate synthesis
- Product Name:tert-butyl 1-(4-chlorophenyl)-2-hydroxyethylcarbaMate
- CAS Number:147353-95-5
- Molecular formula:C13H18ClNO3
- Molecular Weight:271.74
179811-64-4
24424-99-5
147353-95-5
Step 1: Synthesis of tert-butyl (racemic)-(1-(4-chlorophenyl)-2-hydroxyethyl)carbamate: (Racemic)-2-amino-2-(4-chlorophenyl)ethanol (2 g, 1.65 mmol, prepared according to the method described in WO2009/47563A1) was dissolved in THF (20 ml), and di-tert-butyl dicarbonate (Boc anhydride. 2.84 ml, 12.24 mmol) and triethylamine (2.436 ml, 17.48 mmol). The reaction mixture was stirred at room temperature and kept overnight. After completion of the reaction, the mixture was concentrated in vacuum and extracted by dilution with ethyl acetate (EtOAc) and 1N hydrochloric acid (HCl). The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated in vacuum to give the title compound as a viscous solid (2.8 g, 88% yield).1H NMR (500 MHz, CDCl3) data were as follows: δ 7.34 (2H, m), 7.27 (1H, d), 5.35 (1H, m), 4.75 (1H, m), 4.75 (1H, m). 3.75-3.90 (2H, m), 1.44 (9H, s).
179811-64-4
43 suppliers
$119.17/0.25g
24424-99-5
796 suppliers
$13.50/25G
147353-95-5
29 suppliers
$114.00/250mg
Yield:147353-95-5 88%
Reaction Conditions:
with triethylamine in tetrahydrofuran at 20;
Steps:
105.1
Step 1: (rac)-tert-butyl (1 -(4-chlorophenyl)-2-hydroxyethyl)carbamate:To a solution of (rac)-2-amino-2-(4-chlorophenyl)ethanol (2 g, 1 1 .65 mmol) (prepared as described WO2009/47563 A1 ) in THF (20 ml) was added Boc anhydride (2.84 ml, 12.24 mmol) followed by triethylamine (2.436 ml, 17.48 mmol) . The reaction mixture was then stirred at RT and maintained at this temperature overnight. The reaction mixture was concentrated in vacuo, diluted with EtOAc and 1 N HCI and extracted. The organic extracts were then washed with brine, dried (Na2S04) and concentrated in vacuo affording the title compound as a sticky solid (2.8 g, 88%). 1H NMR (500 MHz, CDCI3): 7.34 (2H, m), 7.27 (1 H, d), 5.35 (1 H, m), 4.75 (1 H, m), 3.75- 3.90 (2H, m), 1 .44 (9H, s).
References:
WO2012/69852,2012,A1 Location in patent:Page/Page column 137-138
24424-99-5
796 suppliers
$13.50/25G
6212-33-5
336 suppliers
$6.00/5g
147353-95-5
29 suppliers
$114.00/250mg