Sodium hydride → HCID 59383070, compound

A flame dried 250 mL round bottom flask was charged with sodium hydride (60% in oil, 1.45 g, 36.2 mmol) and trimethyloxosulfonium iodide (8.05 g, 36.5 mmol). The flask was evacuated and refilled with N2. Dry DMSO (50 mL) was added and the mixture was stirred at rt for 1 h. A portion of this solution (14.5 mL, 10.5 mmol, 1.5 equiv) was added by syringe to a 150 mL round bottom flask which had been charged with (R)-tert-butyl 3-(3-chlorobenzoyl)-piperidine-1-carboxylate (2.27 g, 7 mmol) and THF (30 mL) and placed under N2. The resulting mixture was stirred for 1 h at rt. The reaction mixture was quenched with brine and extracted with EtOAc (3×). The combined organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give (3R)-tert-butyl 3-(2-(3-chlorophenyl)oxiran-2-yl)piperidine-1-carboxylate as a mixture of two isomers (2.32 g, 6.9 mmol, 99% yield), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): 1.40 (s, 9H), 1.55-1.72 (m, 3H), 1.85 (m, 1H), 2.01 (m, 1H), 2.35-2.60 (m, 2H), 2.65 (d, 1H), 3.063 (d, 1H), 4.05 (m, 1H), 4.15 (m, 1H), 7.26 (m, 3H), 7.34 (s, 1H); MS (E/Z): 338 (M+H+)

1. customA flame dried 250 mL round bottom flask
2. customThe flask was evacuated
3. additionrefilled with N2
4. additionDry DMSO (50 mL) was added
5. stirringThe resulting mixture was stirred for 1 h at rt
6. customThe reaction mixture was quenched with brine
7. extractionextracted with EtOAc (3×)
8. washThe combined organic phase was washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-ad6f373e4c694800b80558e6cbc6ebef

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858624B2