Nitromethane → HCID 86722944, Verbindung

A sealable reaction tube was charged with 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.16 mL, 0.450 mmol) and THF (1.0 mL) under Argon. Nitromethane (0.23 mL, 4.24 mmol) was added and the reaction stirred at room temperature for 5 min then cooled to 0° C. for 15 min. [4-(tert-Butoxycarbonylamino-methyl)-cyclohexylidene]-acetic acid ethyl ester (0.261 g, 0.878 mmol) in THF (1.5 mL) was added slowly and the reaction stirred at RT for 15 min. The tube was sealed and the reaction heated at 70° C. for 17 hr. The reaction was cooled to room temperature, quenched with 0.5M HCl, and extracted with EtOAc (2×). The combined organic layers were washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated to provide 0.304 g of crude product which was carried to the next step without purification. ESI-MS m/z 359 (MH)+.

1. additionwas added slowly
2. stirringthe reaction stirred at RT for 15 min
3. customThe tube was sealed
4. temperaturethe reaction heated at 70° C. for 17 hr
5. temperatureThe reaction was cooled to room temperature
6. customquenched with 0.5M HCl
7. extractionextracted with EtOAc (2×)
8. washThe combined organic layers were washed with saturated NaHCO3 and brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated

ORD-Eintrag

ord-ae8fbf8424184da8b4744cac269179c7

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09422314B2