Yield:-

Reaction Conditions:

with methanol;potassium carbonate at 20; for 1 h;

Steps:

4

Example 4; Synthesis of (4-ethynyl-benzyl)-methyl-carbamic acid methyl ester (5); Carbamate 4 from step 3 was dissolved in methanol (630 ml). Potassium carbonate (10.5 g, 0.08 mol) was added. The reaction mixture was stirred at room temperature for 1 hour. TLC analysis indicated the completion of the reaction. White solid was filtered off. Methanol was removed by distillation under reduced pressure to afford yellow oil. The oil was further purified by column chromatography (silica gel, hexane/EtOAc) to yield 50.2 g of compound 5 (60% yield over two steps from amine 3). ¹H NMR (300 MHz, CDCl₃) δ 2.85(d, br, 3H), 3.068(s, 1H), 3.744(s, 3H), 4.468(s, br, 2H), 7.195(s, br, 2H), 7.46(d, 2H, J=8.1 Hz). Exact mass calculated for C₁₂H₁₄NO₂: 204.1025. Found: 204.1022.

References:

US2006/63926,2006,A1 Location in patent:Page/Page column 5; 8