Triethylamine → Benzyl 3-hydroxyazetidine-1-carboxylate

A solution of 1-benzhydryl-3-hydroxyazetidine (10 g, 41.8 mmol) in methanol (300 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium (10 g) on charcoal in a water bath (50° C.) for 3 hours. After checking the completion of the reaction, the reaction mixture was filtered and the residue washed with methanol. The combined filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure, and the obtained residue dried under reduced pressure. The resulting crude product was dissolved in a mixture of methylene chloride (120 ml) and methanol (120 ml), chloroformic acid benzyl ester (8.95 ml, 62.7 mmol) and triethylamine (8.79 ml, 62,7 mmol) were added thereto, and the mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The obtained organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1)→ethyl acetate as the eluant to afford 1-benzyloxycarbonyl-3-hydroxyazetidine (1.91 g, yield 22%).

1. customthe completion of the reaction
2. filtrationthe reaction mixture was filtered
3. washthe residue washed with methanol
4. concentrationThe combined filtrate was concentrated under reduced pressure
5. customThe residue was partitioned between ethyl acetate
6. distillationdistilled water
7. concentrationThe organic layer was concentrated under reduced pressure
8. customthe obtained residue dried under reduced pressure
9. additionwere added
10. customthe completion of the reaction
11. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
12. washThe obtained organic layer was washed with saturated aqueous sodium chloride solution
13. dry with materialdried over anhydrous sodium sulfate
14. filtrationfiltered
15. concentrationconcentrated under reduced pressure
16. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-ea5aba3791a54d5c906b7b2170f140d0

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2