Diethyl Ether → (1-Acetyl-cyclobutyl)-carbamic acid tert-butyl ester

Temperatur

25 °C

To a solution of [1-(methoxy-methyl-carbamoyl)-cyclobutyl]-carbamic acid tert-butyl ester (11.5 g, 44.6 mmol) in THF (150 mL) at 0° C. was slowly added methylmagnesium bromide as a 3.0M solution in ether (37.2 mL, 111 mmol). The reaction was allowed to slowly warm to 25° C. and stirred for 24 h then quenched by the addition of saturated aqueous NH4Cl (100 mL). EtOAc (200 mL) was added and the layers were separated. The aqueous phase was extracted two more times with EtOAc. The organic layers were combined, washed with brine, dried (Na2SO4), decanted and concentrated to afford a solid. The solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane) to afford (1-acetyl-cyclobutyl)-carbamic acid tert-butyl ester as a white solid (6.02 g, 63%).

1. customat 0° C.
2. customthen quenched by the addition of saturated aqueous NH4Cl (100 mL)
3. additionEtOAc (200 mL) was added
4. customthe layers were separated
5. extractionThe aqueous phase was extracted two more times with EtOAc
6. washwashed with brine
7. dry with materialdried (Na2SO4)
8. customdecanted
9. concentrationconcentrated
10. customto afford a solid
11. customThe solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane)

ORD-Eintrag

ord-ad3613ba72dd465d82a8cb1a46652f17

Quelldatensatz

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08575360B2