Diethyl Ether → 1257639-06-7
Reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:12](=[O:17])N(OC)C)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][Mg]Br.CCOCC>C1COCC1>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:12](=[O:17])[CH3:19])[CH2:9][CH2:10][CH2:11]1)([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
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%).
Workup
- customat 0° C.
- customthen quenched by the addition of saturated aqueous NH4Cl (100 mL)
- additionEtOAc (200 mL) was added
- customthe layers were separated
- extractionThe aqueous phase was extracted two more times with EtOAc
- washwashed with brine
- dry with materialdried (Na2SO4)
- customdecanted
- concentrationconcentrated
- customto afford a solid
- customThe solid was purified via normal phase flash chromatography on silica gel (10-50% EtOAc-heptane)
Sources & evidence
- ORD record
- ord-ad3613ba72dd465d82a8cb1a46652f17
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575360B2
Reaction notes
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