2-Benzyloxirane, (R)- → 1'-[(2R)-2-hydroxy-3-phenylpropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Participants

Reaction Steps

Compound 186 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, (2R)-2-benzyloxirane and conditions outlined in procedure Y. M.p.=82-84° C.; 400 MHz 1H NMR (DMSO) δ: 7.92-7.88 (m, 1H), 7.8-7.74 (m, 2H), 7.6-7.52 (m, 1H), 7.3-7.14 (m, 5H), 4.44 (brd, J=4.4 Hz, 1H), 3.9-3.8 (m, 1H), 3.07 (s, 2H), 2.82-2.7 (m, 3H), 2.64-2.56 (m, 1H), 2.46-2.28 (m, 4H), 2.04-1.94 (m, 2H), 1.88-1.76 (m, 2H); LCMS: 436 [M+H]; enantiomeric excess determined from chiral HPLC: >99%; Chiral HPLC Rt=50.74 min.

Provenance & Evidence