Triisopropylsilyl chloride → (R)-1-(2-Methoxy-4-nitro-phenyl)-3-triisopropylsilanyloxy-pyrrolidine

Participants

Reaction Conditions

Reaction Steps

Dissolve the crude (R)-1-(2-methoxy-4-nitro-phenyl)-pyrrolidin-3-ol (10.9 g, 45.5 mmol) in dry pyridine (50 mL) and chill to 0° C. Add chloro-triisopropyl-silane (19.8 mL, 91 mmol) dropwise and then heat to 80° C. overnight. Remove the pyridine via reduced pressure and then wash the crude material with NaHSO3 solution and extract with EtOAc (3×100 mL). Combine the organic solutions, then dry and concentrate to give the crude product. Purify over a silica plug with hexanes (300 mL) and flush with 10% EtOAc in hexanes (800 mL) to give the title compound as a reddish oil (17.85 g, 99%). MS (ES+) 395.2 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 7.81 (dd, J=8.8, 2.2 Hz, 1H), 7.63 (d, J=2.2 Hz, 1H), 6.45 (d, J=88 Hz, 1H), 4.57-4.52 (m, 1H), 3.84 (s, 3H), 3.84-3.78 (m, 1H), 3.72-3.64 (m, 1H), 3.61-6.53 (m, 1H), 3.45 (dd, J=11.0, 2.2 Hz, 1H), 2.06-1.92 (m, 2H), 1.04-1.01 (m, 21H).

Provenance & Evidence