Hydrochloric Acid → 4-[2-[1-(2-Hydroxyethyl)cyclohexyl]ethyl]morpholine
Reaction equation
Cl.[O:2]([CH2:20][CH2:21][C:22]1([CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>CO>[OH:2][CH2:20][CH2:21][C:22]1([CH2:28][CH2:29][N:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1Participants
4
Procedure
After adding concentrated hydrochloric acid (0.5 mL, 6.0 mmol) to a solution of 4-[2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl]morpholine (1.31 g, ca. 1.97 mmol) in methanol (10 mL) at room temperature, the mixture was stirred for 4.5 hours. The reaction mixture was then concentrated under reduced pressure, 1N hydrochloric acid (10 mL) was added to the obtained residue, and extraction was performed with diethyl ether. After adding 5N aqueous sodium hydroxide to the aqueous layer to adjust the pH to 12, extraction was performed with diethyl ether. The organic layer was dried (anhydrous sodium sulfate) and then the solvent was distilled off under reduced pressure to obtain the title compound as a colorless oil (448 mg) (94% yield, 2 steps).