Potassium tert-butoxide → 1-(3-Benzyloxy-propyl)-4a-(4-chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-1H-9-oxa-1-aza-phenanthrene

Participants

Reaction Steps

The Methanesulfonic acid 3-{(3-benzyloxy-propyl)-[4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-yl]-amino}-propyl ester was dissolved in 60 mL of THF then potassium tertbutoxide (1M solution in tertbutanol, 3.27 ml, 3.27 mmol) was added and the reaction was stirred at room temperature for 1 h. The reaction was quenched with 100 ml of brine and 100 ml of ethyl acetate. The layers were separated and the organic layer was dried over sodium sulfate then concentrated. The product was purified by column using EtOAc/Hex. as the eluent (gradient from 0/100 to 100/0 in 35 minutes). Yield: 438.8 mg, 80. 1H NMR (CDCl3 400 MHz) δ7.61 (d, J=8.1 Hz, 2H), 7.48 (d, J=8.8 Hz, 2H), 7.37-7.24 (m, 5H), 7.04 (td, 9.5, 5.1 Hz, 1H), 6.43-6.36 (m, 1H), 5.14 (d, J=12.4 Hz, 1H), 4.72 (d, J=13.9 Hz, 1H), 4.47 (dd, J=28.5, 11.7 Hz, 2H), 3.42 (t, J=6.2 Hz, 2H), 3.29 (s, 1H), 2.90-2.82 (m, 2H), 2.82-2.75 (m, 1H), 2.57 (d, 12.4 Hz, 1H), 2.45 (td, J=11.7, 2.2 Hz, 1H), 2.03-1.93 (m, 1H), 1.83-1.64 (m, 2H), 1.63-1.59 (m, 1H), 1.36-1.23 (m, 1H).

Provenance & Evidence