Triethylamine → HCID 10849051, compound

Triethylamine (3.07 ml, 22.02 mmol) was added to a methylene chloride (40 ml) solution of 4-(S)-fluoromethyl-3-(R)-hydroxy-N-[1-(R)-phenylethyl]-2-pyrrolidone (2.61 g, 11.00 mmol), methanesulfonyl chloride (1.28 ml, 16.54 mmol) was added dropwise to the thus prepared solution at −10° C. and then the resulting mixture was stirred for 30 minutes at the same temperature. The reaction solution was washed with 10% citric acid aqueous solution and dried over sodium sulfate and then the solvent was evaporated. The thus obtained residue was dissolved in N,N-dimethylformamide (80 ml), mixed with sodium azide (2.86 g, 44.00 mmol) and then stirred overnight at 100° C. The reaction solution was mixed with water, extracted with ethyl acetate (200 ml×3) and then the resulting organic layers were combined and dried over sodium sulfate, subsequently evaporating the solvent. The thus obtained residue was subjected to a silica gel chromatography to give 1.81 g (63%) of the title compound from the eluate of ethyl acetate:hexane=1:3 in the form of a light yellow oil.

1. additionwas added dropwise to the thus prepared solution at −10° C.
2. washThe reaction solution was washed with 10% citric acid aqueous solution
3. dry with materialdried over sodium sulfate
4. customthe solvent was evaporated
5. dissolutionThe thus obtained residue was dissolved in N,N-dimethylformamide (80 ml)
6. stirringstirred overnight at 100° C
7. extractionextracted with ethyl acetate (200 ml×3)
8. dry with materialdried over sodium sulfate
9. customsubsequently evaporating the solvent

ORD record

ord-e5db1755059d46ff8bc5c0ceb7f43494

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06656952B2