Methanol → tert-Butyl [(3-oxocyclobutyl)methyl]carbamate

Temperature

-78 °C

In a round bottom flask were placed 9 g of the product from Step A of Example 9, 100 mL of methanol, and 400 mL of dichloromethane. The solution was cooled to -78° C., and ozone was bubbled through the reaction mixture until the solution was blue. The system was flushed with nitrogen for 2.5 h, and then treated with 34 mL of dimethylsulide. After 1 h at -78° C., 0° C. for 1 h, and room temperature for 1 h, the solution was stored in a refrigerator at 5° C. overnight before being concentrated. The crude material was purified by column chromatography to afford the title compound.

1. customIn a round bottom flask were placed
2. customozone was bubbled through the reaction mixture until the solution
3. customThe system was flushed with nitrogen for 2.5 h
4. additiontreated with 34 mL of dimethylsulide
5. wait0° C. for 1 h
6. waitroom temperature for 1 h
7. waitthe solution was stored in a refrigerator at 5° C. overnight
8. concentrationbefore being concentrated
9. customThe crude material was purified by column chromatography

ORD record

ord-24eebc7913134719814d09f4259c412d

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05246931