Triethylamine → HCID 86590872, Verbindung

To a solution of (3R)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (9.0 g, 33.8 mmol) in methylene chloride (270 ml) were added methanesulfonyl chloride (2.88 ml, 37.2 mmol) and triethylamine (5.21 ml, 37.2 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the mixture was stirred at room temperature for 1.5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The 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 (1:2)→ethyl acetate as the eluant to afford (3R)-3-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)-pyrrolidine (11.5 g, yield 99%) as a pale yellow solid.

1. customthe completion of the reaction
2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
3. washThe organic layer was washed with saturated aqueous sodium chloride solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography on a silica gel column

ORD-Eintrag

ord-75b62a85cf1248bf8e9fd9bf284b405b

Quelldatensatz

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07001897B2