(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine → (3S)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine

Participants

Reaction Conditions

Reaction Steps

The title compound was synthesized as described for Intermediate example I-3 in 67% yield, starting from (3S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine using 47 w % of 10% palladium on charcoal. The reaction mixture was heated to 55° C. for 1.5 h; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.19 (dd, 1 H), 7.04 (t, 1 H), 6.83 (dd, 1 H), 4.00-4.06 (m, 1 H), 3.50-3.59 (m, 1 H), 3.14-3.23 (m, 1 H), 2.98-3.12 (m, 1 H), 2.52-2.60 (m, 1 H), 1.29 (s, 12 H), 1.06 (s, 2 H); MS (APPI/APCI) m/z 276[M+H+].

Provenance & Evidence