Isopropanol → HCID 178453348, compound

(2-Cyano-ethyl)-carbamic acid tert-butyl ester (59.5 g, 0.35 mol) is dissolved in dry m-xylene 460 ml) and stirred at room temperature. Azidotributyltin (140 g, 0.42 mol) is added and the reaction mixture is heated to 115° C. overnight. On cooling to room temperature, the reaction mixture is quenched with 2M NaOH (500 ml), the layers are separated and the aqueous phase is acidified with 6M HCl to pH 2 resulting in a thick precipitate. DCM (500 ml) is added followed by IPA (50 ml) resulting in clear layers, the organic layer is separated and the aqueous is re-extracted with 9:1 DCM/IPA (2×250 ml). The organic layers are combined, washed with brine (500 ml), dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is triturated with iso-hexanes (250 ml), stirred for 1 hour at room temperature then a further 1 hour at 5-10° C., filtered and dried under vacuum to afford the title compound.

1. temperaturethe reaction mixture is heated to 115° C. overnight
2. temperatureOn cooling to room temperature
3. customthe reaction mixture is quenched with 2M NaOH (500 ml)
4. customthe layers are separated
5. customresulting in a thick precipitate
6. customresulting in clear layers
7. customthe organic layer is separated
8. extractionthe aqueous is re-extracted with 9:1 DCM/IPA (2×250 ml)
9. washwashed with brine (500 ml)
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customThe resulting solid is triturated with iso-hexanes (250 ml)
14. stirringstirred for 1 hour at room temperature
15. filtrationa further 1 hour at 5-10° C., filtered
16. customdried under vacuum

ORD record

ord-9a6b7f49e333473eaafdf4f6da7cc591

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08053574B2