Benzylamine → HCID 58504674, compound
Reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH:12]([CH3:13])[CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:13][CH:12]1[CH2:11][CH:10]([C:14]([NH:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:16])[CH2:9][N:8]1[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-3-pyrrolidinecarboxylic acid (0.9 g, 3.93 mmol) in CH2Cl2 (15 mL) at room temperature was added Hunig's base (0.89 mL, 5.10 mmol, 1.3 equiv) and benzylamine (0.56 mL, 5.10 mmol, 1.3 equiv) in one portion. The resulting mixture was chilled in an ice bath, followed by addition of HATU (1.64 g, 4.32 mmol, 1.1 equiv) in one portion, and the reaction mixture was stirred in the ice bath for 30 minutes. The mixture was filtered through celite, and rinsed with CH2Cl2. The filtrate was washed with water and dried over Na2SO4, followed by filtration and concentration in vacuo. The resulting residue was purified by silica gel column chromatography resulting in 1.70 g of the title compound as an oil. The ratio of cis/trans isomers could not be determined. LC-MS (ES) m/z=319 [M+H]+.
Workup
- temperatureThe resulting mixture was chilled in an ice bath
- filtrationThe mixture was filtered through celite
- washrinsed with CH2Cl2
- washThe filtrate was washed with water
- dry with materialdried over Na2SO4
- filtrationfollowed by filtration and concentration in vacuo
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-3757bc4ce67a47aeab5fe6e97d70ac83
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697685B2
Reaction notes
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