Water → HCID 57803569, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(aminomethyl)-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-4,6-diol (277 mg) in DCM (10 mL) was slowly added to sodium borohydride (200 mg) in 4 mL of TFA-acetic acid, 1:1 at 0° C. The mixture was stirred at 0° C. for 2 h then poured into water and separated the DCM. The DCM was dried and evaporated. The residue was purified by silica gel column eluting with 7.5% MeOH in DCM to give 4-(aminomethyl)-5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-6-ol (55 mg). 1H-NMR (300 MHz, CDCl3): δ=6.12 (s, 1H), 3.78 (s, 2H), 2.34-1.70 (3s+m, 18H) ppm. 13C-NMR (75 MHz, CDCl3): δ146.59, 145.56 137.14, 128.02, 124.51, 123.45, 120.62, 117.21, 76.24, 45.56, 36.07, 14.65, 12.85, 12.56, 12.33 ppm. MS: (m/z): 260 (M+H+).

Provenance & Evidence