3-(Dimethylamino)-1,2-propanediol

pale yellow solid

General procedure: Sodium hydride (38.6 mmol, 1.54 g, 60percent in oil) was charged in a 250 mL two-neck RB flask under nitrogen atmosphere and anhydrous THF (20 mL) was added to remove oil. The resulting suspension was stirred for 10 minutes and then the stirring was stopped to settle the sodium hydride solids. The supernatant liquid was removed with syringe and a fresh THF (100 mL) was added. To this slurry, a solution of 3-(dimethylamino)-propane-1, 2-diol (14.9 mmol, 1.77 g) in THF (15 mL) was added dropwise for 10 minutes at RT. The resulting suspension was heated to reflux for 24 h. Then, a solution of methanesulfonic acid dodecyl ester (38.6 mmol, 10.2 g) in THF (22 mL) was added and again the mixture was heated to reflux for 5 days. Then, it was cooled to RT and the mixture was filtered through a 3-cm plug of celite while washing with ethyl acetate (1.0 L). The filtrate was removed under vacuum and the residue was partitioned between diethyl ether (250 mL) and 0.2M aqueous sodium hydroxide solution (250 mL). The two layers were separated and the organic layer was washed with water (200 mL), brine solution (200 mL), and dried over anhydrous magnesium sulfate. Filtration and concentration gave the light brown oil (7.93 g) which was purified using an ISCO (150 g) flash column chromatography to obtain 4.51 g (67percent yield) of (rac)-2, 3-bis(dodecyloxy-propyl)-N, N-dimethyl-amine as a light yellow oil. ES(+)-HRMS m/e calcd. for C29H61NO2 (M+H)+ 456.4775, obsd. 456.4785.Dodecanedioic acid 2-(11-tert-butoxycarbonyl-undecanoyloxy)-3-dimethylamino-propyl ester tert-butyl ester (33) To an ice-cold solution of 26 (4.6 g, 16 mmol), 3-dimethylamino-propane-1, 2-diol (0.9 mL, 7.6 mmol) and DMAP (catalytic amount) in DCM (40 mL) was slowly added a solution of DCC (4 g, 20 mmol) in DCM (10 mL). After the addition, the solution was warmed to room temperature and stirred for 2 days. The reaction mixture was then filtered to remove the insoluble DCU. Concentration of the filtrate followed by chromatography (50percent EtOAc/DCM to 100percent EtOAC) afforded 2.3 g (46percent yield) product as colorless oil. The characterization data were consistent with the chemical structure and formula.

Molecular Weight:119.16
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:119.094628657
Monoisotopic Mass:119.094628657
Topological Polar Surface Area:43.7
Heavy Atom Count:8
Complexity:56.4
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes