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tert-butyl 1-(4-chlorophenyl)-2-hydroxyethylcarbaMate synthesis

2synthesis methods
-

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