Synthesis
The general procedure for the synthesis of (S)-1-BOC-3-hydroxymethylpyrrolidine from di-tert-butyl dicarbonate and compound (CAS:1264942-79-1) was as follows:
1. 1-[(1S)-1'-phenylethyl]pyrrolidine (8.81 g, 27.6 mmol) was dissolved in 1,2-dichloroethane (75 ml) at room temperature and 1-chloroethyl chloroformate (8.1 ml, 75 mmol) was added to this solution.
2. The resulting mixture was refluxed for 5 hours and then cooled to room temperature.
3. diisopropylethylamine (2.3 ml, 13 mmol) was added to the cooled brown solution and the mixture was refluxed again for 3 hours.
4. After completion of the reaction, the mixture was concentrated and the residue was diluted with ethyl acetate and washed with 1N aqueous hydrochloric acid.
5. The organic layer was dried with anhydrous sodium sulfate and subsequently concentrated under reduced pressure.
6. The residue was dissolved in methanol, an aqueous 1N hydrochloric acid solution was added and the aqueous solution was washed with ethyl acetate.
7. The aqueous solution was alkalized with solid potassium carbonate and the alkaline solution was cooled to 0 °C.
8. tert-Butyl dicarbonate (6.3 g, 29 mmol) was added to tetrahydrofuran (75 ml) at 0 °C.
9. The resulting mixture was stirred for 3 hours and then the organic material was extracted with ethyl acetate.
10. The organic layer was dried with anhydrous sodium sulfate and the solvent was removed under reduced pressure.
11. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 3/1 to 1/2) to afford tert-butyl 3-hydroxymethylpyrrolidine-1-carboxylate (2.96 g, 14.7 mmol, 53%) as a colorless oil.
![Pyrrolidine, 3-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-[(1R)-1-phenylethyl]-, (3S)-](/CAS/20210305/GIF/1264942-79-1.gif)
