(R)-1-(2-Methoxy-4-nitro-phenyl)-3-triisopropylsilanyloxy-pyrrolidine → (R)-3-Methoxy-4-(3-triisopropylsilanyloxy-pyrrolidin-1-yl)-phenylamine

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Reaction Steps

Dissolve (R)-1-(2-Methoxy-4-nitro-phenyl)-3-triisopropylsilanyloxy-pyrrolidine (12 g, 30.4 mmol) in EtOH (200 mL) and add 5% Pd/C (1.26 g). Purge the black mixture with hydrogen (1 atm) and stir overnight under a hydrogen atmosphere at ambient temperature at 60 psi. Filter the black mixture through Celite® and wash the solids with additional EtOH (100 mL). Concentrate the filtrate to give the title compound as a dark brown oil. 1H NMR (400 MHz, CDCl3): δ 6.76 (d, 1H, J=8.8 Hz), 6.31 (d, 1H, J=2.6 Hz), 6.25 (dd, 1H, J=8.8, 2.6 Hz), 3.74 (s, 3H), 1.34 (s, 9H). Note: title compound decomposed rapidly. Store compound in freezer immediately after use. MS (ES+) 365.2 (M+1)+.

Provenance & Evidence