3-Cyanophenol → HCID 22857710, compound

Participants

Reaction Steps

A 1.5 g (20 mmol) sample of (S)-1-BOC-2-pyrrolidinemethanol (from Example 1a) and 3.57 g (30 mmol) of 3-cyanophenol (Aldrich) were added to a complex of TPP and DEAD, (prepared as in Example 5b above, 30 mmol of each) in 100 mL of THF. The reaction was stirred for 16 hr, the solvents were removed under vacuum, and the residue was extracted with hexane and chromatographed on silica gel, eluting with 100:0-85:15 hexane:ethyl acetate to give 2.71 g of the title compound. MS: 303 (M+H)+, 320 (M+NH4)+. NMR (CDCl3) δ: 1.48 (s, 9H), 1.84-2.05 (m, 4H), 3.35-3.45 (br, 2H), 3.75-3.95 (m, 1H), 4.05-4.18 (br, 2H), 7.25-7.40 (m, 4H).

Provenance & Evidence