(3aR,5R,7aS)-5-benzyloxymethyl-7a-(2-fluorophenyl)hexahydropyrano[3,4-c]isoxazole → [(2R,4R,5S)-5-amino-2-benzyloxymethyl-5-(2-fluorophenyl)tetrahydropyran-4-yl]methanol

Participants

Reaction Steps

Compound C14 was prepared from (3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(2-fluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C13) according to the general procedure for the synthesis of [(3S,4R)-3-amino-3-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol (C11) in Example 1. The product was used directly in the following step. LCMS m/z 346.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.65 (ddd, J=14.0, 4.3, 2.5 Hz, 1H), 2.01-2.14 (m, 1H), 2.32-2.41 (m, 1H), 3.35 (dd, J=11.5, 2.9 Hz, 1H), 3.47-3.61 (m, 3H), 3.66 (dd, J=10.2, 6.6 Hz, 1H), 3.84-3.92 (m, 1H), 4.27 (dd, J=11.5, 2.0 Hz, 1H), 4.61 (AB quartet, JAB=12.1 Hz, ΔνAB=25.1 Hz, 2H), 7.06 (ddd, J=13.0, 8.1, 1.3 Hz, 1H), 7.20-7.26 (m, 1H), 7.28-7.41 (m, 6H), 7.64-7.72 (m, 1H).

Provenance & Evidence