Tetrahydrofuran → Diphenyl phosphite

and triflate 13 isomer A (70 mg, 0.167 mmol) in THF (2 mL) was added Cs2CO3 (72 mg, 0.222 mmol). After the reaction mixture was stirred for 30 min at room temperature, the mixture was partitioned between EtOAc and water. The organic phase was dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude product was chromatographed on silica gel (eluting 60-80% EtOAc/hexane) to give a mixture. The mixture was further purified by HPLC on C18 reverse phase chromatography (eluting 55% CH3CN/water) to give phosphonate 14 isomer A (30 mg, 32%) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ 7.71 (d, 2H), 7.26 (m, 6H), 7.00 (m, 5H), 5.65 (d, 1H), 5.14 (m, 1H), 5.00 (m, 2H), 4.54 (dd, 1H), 4.44 (dd, 1H), 4.17 (m, 2H), 3.96 (dd, 1H), 3.86 (m, 5H), 3.72 (m, 3H), 3.14 (m, 1H), 2.97 (m, 4H), 2.79 (m, 2H), 1.83 (m, 1H), 1.62 (m, 3H), 1.50 (d, 3H), 1.25 (m, 3H), 0.93 (d, 3H), 0.88 (d, 3H). 31P NMR (300 MHz, CDCl3) δ 17.4.

1. customthe mixture was partitioned between EtOAc and water
2. dry with materialThe organic phase was dried over Na2SO4
3. filtrationfiltered
4. customevaporated under reduced pressure
5. customThe crude product was chromatographed on silica gel (eluting 60-80% EtOAc/hexane)
6. customto give a mixture
7. customThe mixture was further purified by HPLC on C18 reverse phase chromatography (eluting 55% CH3CN/water)

ORD record

ord-78992ed34f47454b9b5de2e501a3f671

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07649015B2