Diethyl Ether → Racemic-N-(1-(1H-1,2,3-triazol-4-yl)ethyl)-2-methylpropane-2-sulfinamide

N-((1H-1,2,3-triazol-4-yl)methylene)-2-methylpropane-2-sulfinamide (Preparation 64, 2 g, 10 mmol) was dissolved in THF (80 mL) under nitrogen and cooled to −70° C. A solution of methylmagnesium bromide in diethyl ether (3.5M, 7.5 mL, 22.5 mmol) was added dropwise over a period of 15 minutes, keeping the reaction temperature below −60° C. The reaction was stirred with cooling for a further 40 minutes then the cooling bath was removed and the mixture was stirred at room temperature for 18 hours. The reaction was quenched by the addition of saturated aqueous sodium chloride solution (0.5 mL) followed by 2M (aq) HCl (12 mL). The THF was removed in vacuo and the residue acidifed to pH=4 with 2M (aq) HCl. The solution was extracted with EtOAc (110 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 40-100% EtOAc in heptanes to afford the title compound as a 4:1 mixture of diastereomers (1.09 g, 50%).

1. customthe reaction temperature below −60° C
2. temperaturewith cooling for a further 40 minutes
3. customthe cooling bath was removed
4. stirringthe mixture was stirred at room temperature for 18 hours
5. customThe reaction was quenched by the addition of saturated aqueous sodium chloride solution (0.5 mL)
6. customThe THF was removed in vacuo
7. extractionThe solution was extracted with EtOAc (110 mL)
8. dry with materialThe organic layer was dried over anhydrous sodium sulphate
9. concentrationconcentrated in vacuo
10. customThe residue was purified by silica gel column chromatography
11. washeluting with 40-100% EtOAc in heptanes

ORD-Eintrag

ord-db68a73cf00146cda1aa613ec5c1ab2e

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09328096B2