Benzyl Alcohol → HCID 57152973, compound

Temperature

120 °C

To a solution of benzylalcohol (2.0 ml) in DMF (10 ml) was added sodium hydride (60% dispersion in oil, 378 mg), and the mixture was stirred at room temperarture for 1 hour. A solution of (2S)-1-(tert-butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (2.00 g) in DMF (10 ml) was dropwise added thereto, and the mixure was stirred for 4 hours. The reaction mixture was poured into saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluate: hexane-ethyl acetate). Thus-obtained purified compound (640 mg) was dissolved in a mixture of 1,4-dioxane-water (1:1, 30 ml), and barium hydroxide octahydrate (800 mg) was added thereto, and the mixture was refluxed at 120° C. for 4 hours. After the insoluble material was filtered off, the filtrate was adjusted to pH 5-6 with 1M phosphoric acid and washed with ether. The aqueous layer was then adjusted to pH 8 with 1N sodium hydroxide and extracted with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate and concentrated to give crude crystals of the title compound (297 mg).

1. stirringthe mixure was stirred for 4 hours
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated
6. customThe residue was purified by silica gel column chromatography (eluate: hexane-ethyl acetate)
7. customThus-obtained
8. custompurified compound (640 mg)
9. dissolutionwas dissolved in a mixture of 1,4-dioxane-water (1:1, 30 ml), and barium hydroxide octahydrate (800 mg)
10. additionwas added
11. filtrationAfter the insoluble material was filtered off
12. washwashed with ether
13. extractionextracted with chloroform
14. extractionThe chloroform extract
15. dry with materialwas dried over anhydrous magnesium sulfate
16. concentrationconcentrated

ORD record

ord-401b52a602104602b22fec211a91e0a5

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05506256