Formaldehyde → HCID 86605495, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 7-tert-butylspiro[chroman-2,1′-cyclobutan]-6-ol (2.8 g) in dioxane (5 mL) was added an aqueous formaldehyde solution (3.7 mL, 37% in H2O) followed by morpholine (4.0 mL). The reaction was stirred under argon at 90° C. for 2.5 hours, cooled in an ice bath with stirring to precipitate product which was filtered off as a white solid, washed with H20, and air dried to give 7-tert-butyl-5-(morpholinomethyl)spiro[chroman-2,1′-cyclobutan]-6-ol (2.45 g). 1H-NMR (300 MHz, CDCl3) δ=10.74 (s, 1H), 6.73 (s, 1H), 3.77 (br s, 4H), 3.68 (s, 2H), 2.67-2.63 (t, 2H), 2.59 (br s, 4H), 2.29-2.24 (m, 2H), 2.08-1.94 (m, 5H), 1.70-1.65 (m, 1H), 1.40 (s, 9H) ppm. 13C-NMR (75 MHz, CDCl3) δ=150.32, 145.73, 136.19, 118.32, 117.55, 115.00, 76.22, 66.81, 56.78, 52.69, 34.60, 33.91, 29.53, 20.01, 12.46 ppm. MS (m/z)=346 (M+H+), 259 [M-morpholine+H+].

Provenance & Evidence