Lithium borohydride → (2R,4R)-tert-Butyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

2M Lithium borohydride in THF (15.06 ml) was added slowly to a stirred solution of O1-tert-butyl O2-methyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxypyrrolidine-1,2-dicarboxylate (10.35 g) in THF (100 ml) at 0° C. The resulting mixture was allowed to warm to 20° C. and stirred for a further 18 hours. The reaction mixture was quenched with water and evaporated to remove THF. The aqueous residues were extracted with DCM (250 ml). The organic phase was washed sequentially with water (250 ml) and saturated brine (250 ml), dried over Magnesium sulphate, filtered and evaporated to give tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (9.32 g). NMR Spectrum: (DMSOd6) 0.01 (6H, s); 0.80-0.82 (9H, m); 1.34 (9H, s); 1.84-1.89 (1H, m); 1.99 (1H, m); 3.00 (1H, m); 3.53-3.57 (4H, m); 4.28 (1H, s); 4.48-4.49 (1H, m).

1. customThe reaction mixture was quenched with water
2. customevaporated
3. customto remove THF
4. extractionThe aqueous residues were extracted with DCM (250 ml)
5. washThe organic phase was washed sequentially with water (250 ml) and saturated brine (250 ml)
6. dry with materialdried over Magnesium sulphate
7. filtrationfiltered
8. customevaporated

ORD record

ord-0b7e572a059b4607bec4b55817d730b8

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017611B2