tert-butyl 2-(2,2,2-trifluoroethylamino)ethylcarbamate synthesis

Yield:1190890-14-2 44.1 %

Reaction Conditions:

Stage #1: 2,2,2-Trifluoroacetaldehyde;N-BOC-1,2-diaminoethane in dichloromethane at 15;
Stage #2: with sodium cyanoborohydride in dichloromethane at 15;

Steps:

145 tert-butyl (2-((2,2,2-trifluoroethyl)amino)ethyl)carbamate.

To a solution of tert-butyl (2- aminoethyl)carbamate (734 mg, 5.62 mmol, 3.00 eq) in DCM (2.00 mL) was added 2,2,2- trifluoroacetaldehyde (300 mg, 1.87 mmol, 294 uL, 1.00 eq). The resulting reaction mixture was stirred at 15 °C for 3 h. Then, NaBHsCN (235 mg, 3.75 mmol, 2.00 eq) was added, and the reaction mixture was stirred at 15 °C for 1 h before filtering and concentrating under reduced pressure to give a residue. The residue was purified by prep-TLC (SiCh, petroleum ethenEtOAc = 1 : 1) to afford tert- butyl (2-((2,2,2-trifluoroethyl)amino)ethyl)carbamate (200 mg, 825 umol, 44.1% yield) as a colorless oil.

References:

WO2023/283453,2023,A1 Location in patent:Paragraph 0433