4-Morpholineethanol, α-[[[5-methyl-2-(1-methylethyl)cyclohexyl]oxy]methyl]- synthesis

Yield:320784-52-9 44%

Reaction Conditions:

with water at 20; for 18 h;

Steps:

A mixture of compound 1 (200 mg, 0.94 mmol) and morpholine (81.9 mg, 0.94 mmol) in 0.1 mL of water was stirred overnight (about 18 hours) at room temperature. Then, 3 mL of H2O and 5 mL of ethyl acetate was added into the mixture. The organic phase was separated, dried, and concentrated to obtain an oily substance. The crude product was purified by silica gel column (methylene chloride : methanol =30:1) to give 124 mg of title product (^H NMR and MS confirmed, yield 44%) .¹H NMR (400 MHz, CDCl₃) : 3.92-3.83 (m,IH); 3.72-3.60 (m, 5 H); 3.32-3.30 (m, IH); 3.09-3.03(td, J = 10.8, 4.0 Hz, IH); 2.68-2.59 (m, 2H);2.50-2.42 (m, 4H); 2.24-2.16 (m, IH); 2.12-2.07 (m,IH); 1.67-1.59 (m, 2H); 1.38-1.20 (m, 3H); 0.98-0.76(m, 12H) .MS (ESI) calcd for C₁₇H₃₃NO₃ (m/z) : 299.25. found: 300.4 [M+l]⁺

References:

WO2010/51374,2010,A1 Location in patent:Page/Page column 65; 66