2-(2-hydroxyethylamino)ethanol;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Generally in accordance with the procedure described by Ghosh et al in J. Org. Chem. 2004, 69, 7822-7829, tetrahydrofuro[2,3-b]furan-3(2H)-one (950 mg, 7.42 mmol, 1 eq.) was dissolved at 0° C. in 50 mL of ethanol. NaBH4 (302.4 mg, 8 mmol, 1.07 eq.) was added in one portion to the mixture. After a 1 hour stirring period, diethanolamine hydrochloride salt (3.2 g, 8 mmol, 1.07 eq.) was added and the mixture was stirred overnight at room temperature. The heterogeneous mixture was filtered over dicalite and washed with 20 mL of warm AcOEt. After evaporation of the organic solvents under reduced pressure to afford 1500 mg of hexahydrofuro[2,3-b]furan-3-ol with a quality (area %) of 40%; max yield: 60%. diastereoisomeric excess: exo(3S,3aS,6aR)/endo (3R,3aS,6aR): 18.5/81.5. the mixture was stirred overnight at room temperature The heterogeneous mixture was filtered over dicalite washed with 20 mL of warm AcOEt After evaporation of the organic solvents under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 2 L round bottom flask charged with 600 mL of ethanol and NaBH4 (12.55 g, 0.33 mol, 1.1 eq.) at 0° C., ethyl hydroxy-(2-isopropoxytetrahydro-3-furanyl)acetate (70 g, 0.3 mol, 1 eq.) dissolved in 400 mL of ethanol was added dropwise over 1 hour at 0° C. The mixture was allowed to warm up at room temperature and stirred for 19 hours. After cooling at 0° C., diethanolamine hydrochloride (46.7 g, 0.33 mol, 1.1 eq.) dissolved in 100 mL of water was added over 10 min. and stirred for 8 hours. The solvent was evaporated under reduced pressure to afford a clear yellow solid. After dilution with 300 mL of ethylacetate, the heterogeneous mixture was filtered over dicalite. The mixture was used directly in the next step. was added dropwise over 1 hour at 0° C After cooling at 0° C. was added over 10 min. stirred for 8 hours The solvent was evaporated under reduced pressure to afford a clear yellow solid After dilution with 300 mL of ethylacetate, the heterogeneous mixture was filtered over dicalite