Sodium Azide → HCID 54408003, compound

Temperature

110 °C

1-benzyl-4-methanesulfonyloxymethyl-4-hydroxymethyl-pyrrolidine-3-one-O-methyloxime was dissolved in 400 ml of dimethylformamide and thereto 21 g of sodium azide was added and the resulting solution was stirred for 6 hours at 110° C. The reaction mixture was concentrated under the reduce pressure, diluted with 300 ml of ethylether, washed twice with each 200 ml of water and twice with each 200 ml of saline solution, dried with magnesium sulfate, filtered and concentrated under the reduced pressure to give 31 g of 1-benzyl-4-azidomethyl-4-hydroxymethyl-pyrrolidine-3-one-O-methyloxime (yield: 87.3%). The obtained compound and 18 ml of triethylamine were added into 300 ml of dichloromethane and cooled to 0-5° C., and thereto 9.0 ml of methanesulfonylchloride was slowly added by dropping. The reaction temperature was increased up to room temperature and the mixture was stirred for 1 hour. The reaction mixture was washed with 200 ml of water and 200 ml of saline solution, dried with magnesium sulfate, filtered and concentrated under the reduced pressure and the concentrated residue was purified by silicagel column chromatography(ethylacetate:normal hexane=1:3) to give 38.8 g of the titled compound (yield: 98.4%).

1. concentrationThe reaction mixture was concentrated under the reduce pressure
2. additiondiluted with 300 ml of ethylether
3. washwashed twice with each 200 ml of water and twice with each 200 ml of saline solution
4. dry with materialdried with magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under the reduced pressure

ORD record

ord-703927d62dd241a98af725b641bdf220

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06552196B2