Benzylamine → HCID 67969353, Verbindung

Temperatur

0 °C

Triethylamine (0.932 mL, 6.69 mmol) was added to a solution of tert-butyl [(1S,3R)-4-hydroxy-1-(hydroxymethyl)-3-methylbutyl]carbamate (0.39 g, 1.7 mmol) in DCM (7.5 mL) at 0° C. Methanesulfonyl chloride (0.388 mL, 5.01 mmol) was then added dropwise to the resulting solution. After stirring at 0° C. for 1 h, the mixture was diluted with DCM (50 mL), washed with saturated aq. NaHCO3 (50 mL), dried over Na2SO4 and concentrated under reduced pressure. Benzylamine (3.65 mL, 33.4 mmol) was added to the resulting residue and mixture was stirred at 70° C. for 18 h, then cooled to room temperature. The reaction mixture was diluted with EtOAc (100 mL), washed with 10% aq. K3PO4 (50 mL) and brine (50 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (0-30% EtOAc in hexanes) to give the sub-title compound as a white solid (0.34 g, 67%). LCMS calc. for C18H29N2O2 (M+H)+: m/z=305.2. found 305.2.

1. washwashed with saturated aq. NaHCO3 (50 mL)
2. dry with materialdried over Na2SO4
3. concentrationconcentrated under reduced pressure
4. stirringwas stirred at 70° C. for 18 h
5. temperaturecooled to room temperature
6. washwashed with 10% aq. K3PO4 (50 mL) and brine (50 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography on silica gel (0-30% EtOAc in hexanes)

ORD-Eintrag

ord-34a3bb7b848a466f9b0ce57ccc6cc677

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09278950B2