915095-89-5, (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
A solution of 50 gm of (S)-4-bromo-l-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)- benzene in tetrahydrofuran 300 mL and toluene 100 mL was cooled to -90 C to -100 C, 90 mL of n-hexyl Lithium (33% in tetrahydrofuran) was gradually added and the solution was stirred for 15 to 30 min. Then a solution of 2, 3, 4, 6 -tetrakis-0-(trimethylsilyl)-D- glucopyranone in toluene was added at -90 C to -100 C and the reaction mixture was stirred for 2 to 5 hrs. Thereafter 200 mL solution of methanesulphonic acid in methanol was added to the reaction mixture at -70 C to -90 C, the temperature of the reaction mixture was raised to 0 C to 15 C and the reaction mixture was stirred for 10 to 15 hrs at ambient temperature. The solution was then quenched with 8% aq. sodium bicarbonate solution followed by layer separation. The aqueous layer was extracted with ethylacetate (2 X 250 mL).The combined organic layer was washed with 250 mL 10% brine solution. The combined organic layer was concentrated under vacuum followed by stripping with acetonitrile 50mL to afford 95 gm of crude intermediate compound of formula (IV) as an oily mass. 200 mL of dichloromethane and 100 mL of acetonitrile was added to the oily mass at -30 C to -40 C followed by addition of trimethylsilane and borontrifluoride etherate. The reaction mixture was stirred for 2 to 3 hrs followed by addition of 550 mL of 8% aq. sodium bicarbonate solution at 5 C to 20 C. The organic layer was separated and extracted with dichloromethane (I X 250 mL and 1 X 100 mL). The combined organic layer was concentrated to get an oily mass of compound of formula (V). A solution of compound of formula (V) in 200 mL dichloromethane was added to slurry of 50 gm L-proline in 200 mL isopropanol and heated at 40 oC to 50 C for 7-10 hrs. The reaction mixture was filtered and washed with 25 mL dichloromethane and dried under vacuum to afford 53 gm of crystalline Form A of Empagliflozin L-proline complex.
The synthetic route of 915095-89-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; LUPIN LIMITED; AGARKAR, Amit, Madan; MITRA, Rangan; RANANAWARE, Umesh, Babanrao; GODBOLE, Himanshu, Madhav; SINGH, Girij, Pal; (27 pag.)WO2017/141202; (2017); A1;,
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