Water → HCID 68584487, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 1-(iodomethyl)cyclopropanecarboxylate (1.9 g 6.7 mmol, step 1 of Example 3), tert-butyl(piperidin-4-ylmethyl)carbamate (3.0 g, 14 mmol), N,N-diisopropylethylamine (5.8 mL, 34 mmol) in N,N-dimethylformamide (25 mL) was heated at 120° C. for 20 h. After cooled to room temperature, water (50 mL) was added, extracted with ethyl acetate/toluene (1:2, 60 mL×2), washed with water (50 mL×2), brine (50 mL), dried over MgSO4, filtered and concentrated to give brown oil. The oil was chromatographed on a column of silica gel eluting with CH2Cl2/methanol (10:1) to give 560 mg (1%) of the title compound as clear brown oil. MS (ESI) m/z: 369 (M+H)+. 1H-NMR (CDCl3) δ: 4.60 (1H, br), 3.08-2.82 (4H, m), 2.59 (2H, s), 2.10-1.90 (2H, m), 1.75-1.55 (4H, m), 1.50-1.05 (23H, m).

Provenance & Evidence