Dichloromethane → HCID 66795972, compound

Participants

Reaction Steps

A mixture of 30.0 g (86.5 mmol) of 2-[2-(bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 91.0 ml (63.3 g, 865 mmol) of tert-butylamine in 200 ml of THF was stirred at room temperature for 48 h. The resulting mixture was filtered through glass frit (G3) and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 urn; eluent: dichloromethane and then dichloromethane-methanol=1:1, vol.). Yield 27.4 g (94%). Anal. Calc. for C21H30BNO2: C, 74.34; H, 8.91; N, 4.13. Found: C, 74.49; H, 9.09; N, 3.98. 1H NMR (CDCl3): 8.80 (br. s, 1H, NH), 8.53 (m, 1H, 8-H in naphthyl), 7.88 (d, J=8.3 Hz, 1H, 4-H in naphthyl), 7.83 (d, J=8.3 Hz, 1H, 3-H in naphthyl), 7.71 (m, 1H, 5-H in naphthyl), 7.47 (m, 1H, 7-H in naphthyl), 7.41 (m, 1H, 6-H in naphthyl), 4.44 (s, 2H, CH2N), 1.49 (s, 12H, CMe2CMe2), 1.41 (s, 9H, tBu).

Provenance & Evidence