Ammonia → HCID 55297123, compound

Participants

Reaction Steps

Triphenylphosphine (45 g, 0.17 mol, 1.20 eq) was added in portions to a solution of compound (3S*,4R*)-3-azido-4-(4-fluorophenyl)tetrahydrofuran (Preparation 61, 29.6 g, 0.14 mol, 1 eq) in THF (200 mL) on a water bath under stirring for 1 h. The mixture was stirred at room temperature for 2 h, and ammonia 880 (50 mL) was added. The mixture was refluxed for 2 h and cooled. Then concentrated hydrogen chloride (13 mL) was added, and the mixture was evaporated. The residue was diluted with water (150 mL) and extracted with carbon tetrachloride (3×200 mL). Then the aqueous layer was alkalized with the saturated potassium carbonate solution and extracted with chloroform (3×200 mL). The combined organic layer was dried and evaporated to give title compound as a yellow oil (17.82 g, 0.1 mol, 69%).

Provenance & Evidence