Ammonium Chloride → HCID 67979496, compound

Temperature

-15 °C

To a suspension of 5.18 g (27.18 mmol) CuI in 85 mL anhydrous THF at −78° C. was added 24 mL (34 mmol) of a 1.4 M solution of methyl magnesium bromide in THF/toluene dropwise under an atmosphere of nitrogen, the reaction was left to warm up to −15° C. and then stirred at this temperature for 45 minutes. It was cooled again at −78° C. and a solution of 3.85 g (13.59 mmol) 5-oxo-2,5,6,7-tetrahydro-azepine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester in 30 mL anhydrous THF was added dropwise. The resulting reaction mixture was stirred at −78° C. for 30 minutes and then left to warm up to room temperature over a period of 60 minutes. 100 mL saturated aqueous ammonium chloride was added and the resulting mixture was extracted with EtOAc (3×150 mL), the organic layers were combined, washed with H2O (2×200 mL) and saturated brine (200 mL) and dried over MgSO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, hexane/EtOAc 8:2) to give crude material that was used in the next step.

1. waitthe reaction was left
2. temperatureIt was cooled again at −78° C.
3. customThe resulting reaction mixture
4. stirringwas stirred at −78° C. for 30 minutes
5. waitleft
6. temperatureto warm up to room temperature over a period of 60 minutes
7. extractionthe resulting mixture was extracted with EtOAc (3×150 mL)
8. washwashed with H2O (2×200 mL) and saturated brine (200 mL)
9. dry with materialdried over MgSO4
10. filtrationAfter filtration and evaporation of the solvent the product
11. customwas purified by column chromatography (silica, hexane/EtOAc 8:2)
12. customto give crude material that

ORD record

ord-3e984803bba540c6b750dd51c948984d

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346816B2