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With triphenylphosphine on polystyrene; di-tert-butyl-diazodicarboxylate; In tetrahydrofuran; at 20℃; for 16h;
To a solution of 2,7-dihydroxyfluoren-9-one (0.21 g, 1.0 mmol; see Synth. Commun. 1976, 6, 371) and (2R)-(+)-1-Boc-2-pyrrolidinemethanol (0.81 g, 4.0 mmol; Aldrich) in dry THF (10 mL) was added polymer-bound triphenylphosphine (1.3 g, 4.0 mmol; Aldrich) followed by di-tert-butylazodicarboxylate (920 mg, 4.00 mmol; Aldrich). The mixture was stirred overnight (16 h) at room temperature, then filtered through diatomaceous earth, rinsing with ethyl acetate. After concentrating the solution, the residue was purified by flash chromatography (35 g silica gel, 10-30percent ethyl acetate-hexane) to afford the title compound (310 mg, 0.54 mmol; 54percent).
2,7-bis[(2R)-1-boc-pyrrolidin-2-ylmethoxy]-fluoren-9-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
54%
With di-tert-butyl-diazodicarboxylate; polymer-bound triphenylphosphine; In tetrahydrofuran; at 20℃; for 16h;
To a solution of 2,7-dihydroxyfluoren-9-one (0.21 g, 1.0 mmol; see Synth. Commun. 1976, 6, 371) and (2R)-(+)-1-Boc-2-pyrrolidinemethanol (0.81 g, 4.0 mmol; Aldrich) in dry THF (10 mL) was added polymer-bound triphenylphosphine (1.3 g, 4.0 mmol; Aldrich) followed by di-tert-butylazodicarboxylate (920 mg, 4.00 mmol; Aldrich). The mixture was stirred overnight (16 h) at room temperature, then filtered through diatomaceous earth, rinsing with ethyl acetate. After concentrating the solution, the residue was purified by flash chromatography (35 g silica gel, 10-30percent ethyl acetate-hexane) to afford the title compound (310 mg, 0.54 mmol; 54percent). MS (DCl/NH3): m/z 596 (M+18)+.