(S)-1-((S)-2,5-Dihydrofuran-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate → (R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

Alternative preparation of Benzyl (R)-2-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethylcarbamate (18); ‘One-pot’ procedure 3; Aqueous Conditions. (S)-1-((S)-2,5-Dihydrofuran-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate (14) (0.95 g, 3.35 mmol) was suspended in ammonium hydroxide (4 mL) then stirred and heated at 75° C. in a sealed tube for 6 hours during which time the two liquid phases became a single phase solution. The mixture was stirred at ambient temperature for 20 hours then the solvents were removed in vacuo. The residue was azeotroped with diethyl ether (3×10 mL) to obtain (R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol which was used without further purification.

Provenance & Evidence