Ammonium Chloride → (2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate

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Reaction Steps

N,N-Diisopropylethylamine (21.1 ml, 121 mmol) and mesyl chloride (4.67 ml, 60.3 mmol) were successively added to a solution of (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-hydroxymethylpyrrolidine (10.2 g, 30.2 mmol; the compound of Reference Example 1-3) in European Laid Open Patent Application No. 449191) in methylene chloride (200 ml) in a nitrogen stream under cooling with ice and the resulting liquid mixture was stirred at the same temperature for 30 minutes. To this reaction solution, saturated aqueous ammonium chloride was added to terminate the reaction. The reaction mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(mesyloxymethyl)pyrrolidine as the residue.

Provenance & Evidence