HCID 59013462, compound → HCID 46871672, compound

Participants

Reaction Steps

To a solution of (1S,3′R,4′S,5′R,6′R)-3′,4′,5′-tris(benzyloxy)-6′-(benzyloxymethyl)-5-chloro-6-(4-ethylbenzyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran] (120 mg, 0.15 mmol) in methanol (10 mL) was added Pd/C (40 mg, 30% wt). The mixture was stirred under hydrogen (1 atm) for 12 h at room temperature. It was filtered, and the filtrate was concentrated to give a residue, which was purified by preparative HPLC to provide 52 mg (81%) of product as a white solid. 1H NMR (CD3OD, 300 MHz): δ 7.25 (s, 1H), 7.23 (s, 1H), 7.09 (m, 4H), 4.05 (s, 2H), 3.80 (m, 1H), 3.64-3.34 (m, 5H), 2.93 (dd, J=7.8, 6.6 Hz, 2H), 2.58 (q, J=7.8 Hz, 2H), 2.53 (dt, J=13.2, 7.5 Hz, 1H), 2.11 (dt, J=13.2, 7.5 Hz, 1H), 1.19 (t, J=7.8 Hz, 3H); MS ESI (m/z) 419 (M+1)+, calc. 418.

Provenance & Evidence