Diethyl Ether → 1,1-Dimethylethyl 4-(2,4-dichlorophenyl)hexahydro-1H-1,4-diazepine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].Br[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29].C(OCC)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of [1,4]diazepane-1-carboxylic acid tert-butyl ester (0.36 g, 1.77 mmol) in toluene (5 mL) was added tris(dibenzylideneacetone)-dipalladium(0) (0.040 g, 0.044 mmol), R(+)-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.027 g, 0.044 mmol), sodium t-butoxide (0.13 g, 1.33 mmol), and 1-bromo-2,4-dichlorobenzene (0.20 g, 0.89 mmol). The solution was heated to 100° C. for 2 h. The reaction was cooled to room temperature, diethylether (5 mL) was added and the resulting mixture filtered through a bed of diatomaceous earth. The residue was chromatographed on silica gel using hexane/ethyl acetate from 100% to 95% hexane in a gradient fashion, to give the title compound as a gum (0.13 g, 43%). The residue was used as is without further purification.
Workup
- temperatureThe reaction was cooled to room temperature
- filtrationthe resulting mixture filtered through a bed of diatomaceous earth
- customThe residue was chromatographed on silica gel
Sources & evidence
- ORD record
- ord-14014084ed7e4906be61e40a571911af
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935703B2
Reaction notes
Loading…