TERT-BUTYL N,N-BIS(2-HYDROXYETHYL)CARBAMATE

Light yellow clear liquid

To a solution of 2, 2’-azanediyldiethanol (4.21 g, 40 mmol) in acetonitrile (50 mL) was added a solution of Boc2O (9.60 g, 44 mmol) in acetonitrile (50 mL) under N2. The reaction mixture was stirred at rt for 3.5 h, and concentrated in vacuo to give the title compound as colorless oil (8.20 g, 100percent).To a solution of 2, 2'-azanediyldiethanol (4.21 g, 40 mmol) in acetonitrile (50 mL) was added a solution of BocUnder nitrogen protection, 2, 2'-hydroxydiethylamine (4.21 g, 40 mmol) was dissolved in acetonitrile (50 mL) and stirred at room temperature.Boc anhydride (9.60 g, 44 mmol, 50 mL of acetonitrile was dissolved) was added dropwise, and the reaction was complete at room temperature for 3.5 h.After completion of the reaction, the solvent was evaporated under reduced pressure to give a colorless oil (8.20 g, 100percent).To a solution of bis(2-hydroxyethyl) amine (10.0 g, 95.2 mol) in CH2Cl2 (100 mL) at 0 °C was added a solution of Boc2O (22.8 g, 104.5 mmol) in CH2Cl2 (30 mL). After 1.5 h the solution was concentrated in vacuo. The residue was purified by FC on silica gel (Hexanes/EtOAc = 2:1-1:4) to afford tert-butyl bis(2-hydroxyethyl)carbamate 9 (18.45g, 97percent) as a colorless oil.First step: Di-tert-butyl dicarbonate (5.9 g, 27.03 mmol) was added to the mixture in THF, distilled water, and diethanolamine (2.36 ml, 24.90 mmol) four times for 10 minutes. After stirring for 40 minutes, saturated aqueous NaHCO3 solution was added to adjust pH to 8. Thereafter, the mixture was stirred at room temperature for 4 hours and 30 minutes. The reaction was terminated by evaporation of THF, followed by addition of EtOAc, washing with 2.5 M Ammonium chloride and aqueous NaCl solution, and drying over MgSO4. EtOAc was evaporated and redissolved in hexane and evaporated. The reaction product (Boc-2 methylaminoethanol) was dried in a vacuum oven (yield = 92percent).To a stirred solution of diethanolamine (2.50 g, 23.80mmol) in dichloromethane (30 mL), (Boc)

Building block for the synthesis of cationic lipids, nucleosides, etc.

Molecular Weight:205.25
XLogP3:-0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:205.13140809
Monoisotopic Mass:205.13140809
Topological Polar Surface Area:70
Heavy Atom Count:14
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes