反应详情

To a solution of tetrahydro-2H-thiopyran-4-carboxylic acid (2.0 g, 13.7 mmol) in THF (25 mL) was added CDI (2.66 g, 1.20 eq). The mixture was stirred at rt for 1 h. To a solution of LiHMDS (1.0 M in THF, 29 mL) in THF (30 mL) at −78° C. was added EtOAc (2.90 mL) dropwise. The mixture was stirred at −78° C. for 1 h, then the acid/CDI mixture was added through an addition funnel over 30 min at −78° C. The mixture was stirred at −78° C. for 1 h then allowed to warm up to rt over 2 h. The reaction was quenched with saturated NH4Cl and extracted with diethyl ether. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by Biotage (CH2Cl2/EtOAc, 100:1 to 10:1) to give the title compound as a clear oil. LC/MS RT=1.73 min (5 min method). Mass calculated for, M+H 217.08, observed 217.08.

1. stirringThe mixture was stirred at −78° C. for 1 h
2. stirringThe mixture was stirred at −78° C. for 1 h
3. temperatureto warm up to rt over 2 h
4. customThe reaction was quenched with saturated NH4Cl
5. extractionextracted with diethyl ether
6. dry with materialThe combined organic layers were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by Biotage (CH2Cl2/EtOAc, 100:1 to 10:1)