[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol → rel-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol

Participants

Reaction Steps

rel-(3aR,5R,7aS)-5-Cyclopropyl-7a-(2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C19) (1.19 g, 4.23 mmol) was converted to the product according to the method described for the synthesis of [(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol (C6) in Preparation P1. The product was obtained as a thick, pale amber gum (1.22 g), which was taken directly to the following step without additional purification. LCMS m/z 284.1 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 7.61-7.77 (br m, 1H), 6.90-7.05 (br m, 1H), 6.82 (ddd, J=12.7, 8.6, 2.6 Hz, 1H), 4.13 (dd, J=11.5, 2.5 Hz, 1H), 3.55 (br dd, J=11, 2 Hz, 1H), 3.32-3.49 (br m, 2H), 2.89 (ddd, J=11.3, 8.2, 2.5 Hz, 1H), 2.03-2.34 (br m, 2H), 1.81 (ddd, J=14.0, 4.0, 2.6 Hz, 1H), 1.01-1.13 (br m, 1H), 0.53-0.65 (m, 2H), 0.41-0.48 (m, 1H), 0.24-0.32 (m, 1H).

Provenance & Evidence