4-Iodophenol → (R)-2-(4-Iodo-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Beteiligte Stoffe

Reaktionsschritte

To a 250 mL flask which contained a suspension of NaH (60% in mineral oil, 500 mg, 12 mmol) in DMF (50 mL) was added 4-iodo-phenol (2200 mg, 10 mmol), at 0° C. The mixture was allowed to warm to rt and stir at rt for 30 min then cooled to 0° C. To this reaction mixture was added (R)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3600 mg, 10 mmol) at 0° C. The resulting mixture was allowed warm to rt and stir at rt for 30 min and then was heated to 95° C. and stirred at 95° C. for 16 h. After cooling to rt, the mixture was poured onto 2000 mL ice-water solution and this solution was allowed to stir at 0° C. for 30 min. The solid which formed was filtered out, dried through air to afford the title product (2480 mg, 60%); 1H NMR (400 MHz, CDCl3); δ 1.47 (s, 9H), 1.81-2.07 (m, 4H), 3.27-3.48 (m, 2H), 3.70-3.95 (m, 1H), 4.00-4.19 (m, 2H), 6.66-6.69. (m, 2H), 7.53 (d, J=8.4 Hz, 2H):

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