1-Chloroethyl chloroformate → Ethyl acetate methanol ammonium hydroxide

To a stirred solution of 1-benzhydryl-3-(2,4,4′-trichlorobenzhydryloxy)azetidine (3) (39 mmol) in dichloromethane (400 mL) was added 1-chloroethylchloroformate (98 mmol) dropwise at 0° C. and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, then dissolved in methanol (400 mL) and stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo, then diluted with ethyl acetate (400 mL) and washed with sodium hydroxide (5N, 400 mL), dried (MgSO4) and concentrated in vacuo to furnish a yellow oil. The residue was purified by filtration through silica, eluting with dichloromethane, then [ethyl acetate:methanol:ammonium hydroxide (90:8:2)] to yield a yellow oil (8.0 g, 60%).

1. concentrationThe reaction mixture was concentrated in vacuo
2. dissolutiondissolved in methanol (400 mL)
3. stirringstirred at room temperature for 1 hour
4. concentrationThe reaction mixture was concentrated in vacuo
5. additiondiluted with ethyl acetate (400 mL)
6. washwashed with sodium hydroxide (5N, 400 mL)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo
9. customto furnish a yellow oil
10. filtrationThe residue was purified by filtration through silica
11. washeluting with dichloromethane

ORD record

ord-106c1a67238641f0957055dcc6230eb1

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504522B2