Tert-butyl 3-azidoazetidine-1-carboxylate → Tert-butyl 3-aminoazetidine-1-carboxylate

A solution of 3-azido-1-(t-butoxycarbonyl)azetidine (3.44 g, 17.4 mmol) (obtained as described in Reference Example 57(2)) in methanol (170 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (3.44 g) at room temperature for 2 hours. After checking the completion of the reaction, the reaction mixture was filtered in order to remove the catalyst. The filtrate was concentrated under reduced pressure to give 3-amino-1-t-butoxycarbonylazetidine as a crude product. This product was dissolved in methylene chloride (170 ml), and chloroformic acid p-nitrobenzyl ester (5.63 g, 26.1 mmol) and triethylamine (3.66 ml, 26.1 mmol) were added thereto in an ice bath. 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→1:2) as the eluant to afford 1-t-butoxycarbonyl-3-(p-nitrobenzyloxycarbonylamino)azetidine (4.84 g, yield 79%) as a colorless oil.

1. customthe completion of the reaction
2. filtrationthe reaction mixture was filtered in order
3. customto remove the catalyst
4. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-cf30bf626a4548f492eacbd6a91dc493

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2