Ethyl Acetate → HCID 58994950, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[Br:18]N1C(=O)CCC1=O.CCOC(C)=O>C(Cl)Cl.CC#N>[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[C:15]([Br:18])[CH:16]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-(4-amino-phenyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (as prepared in the previous step, 1.65 g, 7.01 mmol) in 100 mL of 1:1 DCM/CH3CN at 0° C. was slowly added N-bromosuccinimide (NBS) (1.25 g, 7.01 mmol) in 25 mL of 1:1 DCM/CH3CN under Ar. After stirring at 0° C. for 0.5 h, the mixture was treated with 50 mL of EtOAc and washed with H2O (2×30 mL) and brine H2O (20 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (1-4% EtOAc/DCM) to give 1.85 g (84%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C13H16BrNO3, 314.0 (M+H). found 314.2.
Workup
- washwashed with H2O (2×30 mL) and brine H2O (20 mL)
- dry with materialThe organic layer was dried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography on silica gel (1-4% EtOAc/DCM)
Sources & evidence
- ORD record
- ord-27fd26295ee745b6aecdaaee8f7faace
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859602B2
Reaction notes
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