反应详情

To a solution of 4-3 (0.25 g, 0.76 mmol) in diethyl ether (3.8 mL) at 0° C. was added a solution of CH2N2 (7.6 mmol, made from treatment of 1-methyl-3-nitro-1-nitrosoguanidine with 40% KOH) in diethyl ether (5 mL) under nitrogen and the reaction mixture was stirred 2 h. The reaction was dried over magnesium sulfate and concentrated directly to yield an oil of >90% purity. The product was used without further purification. The oil was resuspended in THF (1.7 mL) at ambient temperature and to the mixture was added borane-tetrahydrofuran complex in THF (2.4 mL, 2.4 mmol, 1.0M solution). The reaction was stirred 15 h and quenched with methanol (2 mL). The combined organic phase was dried over magnesium sulfate and concentrated. The residue was purified by normal phase silica gel chromatography (0 to 65% EtOAc in hexanes) to afford the product (4-4) as an oil.

1. dry with materialThe reaction was dried over magnesium sulfate
2. concentrationconcentrated directly
3. customto yield an oil of >90% purity
4. customThe product was used without further purification
5. customwas resuspended in THF (1.7 mL) at ambient temperature and to the mixture
6. stirringThe reaction was stirred 15 h
7. customquenched with methanol (2 mL)
8. dry with materialThe combined organic phase was dried over magnesium sulfate
9. concentrationconcentrated
10. customThe residue was purified by normal phase silica gel chromatography (0 to 65% EtOAc in hexanes)