Methanamine, N-methoxy-, hydrochloride (1:1) → (3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide
Reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[CH2:6]([N:13]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH:15]([C:26](O)=[O:27])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH3:5][O:4][N:3]([CH3:2])[C:26]([CH:15]1[CH:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH2:17][N:13]([CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14]1)=[O:27]Participants
7
Reactant 4
HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 16244042(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acidProduct 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N,O-dimethylhydroxylamine hydrochloride (0.41 g, 4.2 mmol) and 1.23 g (3.5 mmol) of (3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid in DMF (20 mL) at RT was added Hunig base (1.79 ml, 10.5 mmol) and HATU (1.468 g, 3.9 mmol) and stirring was continued for one hour. The reaction mixture was diluted with ethyl acetate and washed with aq. ammonium chloride solution three times. The separated organic layer was washed with brine and dried on Na2SO4 and concentrated under vacuo yielding 1.36 g (99%) of the title compound as a light yellow oil. ES-MS m/e: 393.1 (M+H+).
Workup
- washwashed with aq. ammonium chloride solution three times
- washThe separated organic layer was washed with brine
- customdried on Na2SO4
- concentrationconcentrated under vacuo
Sources & evidence
- ORD record
- ord-333141e4ab804dd68be1aeb5cbf4fc29
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012998B2
Reaction notes
Loading…