Water → HCID 69472417, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,5S)-(5-phenyl-pyrrolidin-2-yl)-methanol (0.78 g, 4.4 mmol) in CH2Cl2 (7 mL) at 0° C. was added 0.72 mL (5.2 mmol, 1.2 eq) of Et3N followed by a slow addition of 0.66 mL (5.2 mmol, 1.2 eq) of TMSCl. The mixture was stirred at 0° C. for 45 min. Water (3 mL) was added to quench the reaction. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2 mL×2). The combined organic layer was dried (Na2SO4) and concentrated under vacuum to give 0.98 g (89%) of (2R,5S)-2-phenyl-5-trimethylsilanyloxymethyl-pyrrolidine as a yellow oil. 1H NMR (CDCl3, 300 MHz) δ 7.60–7.30 (5H, m), 4.30 (1H, m), 3.85 (2H, m), 3.50 (1H, m), 2.25 (1H, m), 2.05 (1H, m), 0.25 (9H, m).

Provenance & Evidence