Hydrochloric Acid → 5-Amino-5-benzyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide
Reaction equation
Cl.[CH3:2][N:3]([CH3:24])[C:4]([N:6]1[CH2:10][CH:9]2[CH2:11][C:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([N:14]=C=O)[CH2:13][CH:8]2[CH2:7]1)=[O:5].[OH-].[Na+]>>[CH3:24][N:3]([CH3:2])[C:4]([N:6]1[CH2:10][CH:9]2[CH2:11][C:12]([NH2:14])([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH:8]2[CH2:7]1)=[O:5]Participants
4
Procedure
To a solution of 12 mL hydrochloric acid (8 N) was added dropwise 5-benzyl-5-isocyanato-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 14e obtained from the above step at room temperature. The reaction mixture was stirred for 30 minutes and adjusted to pH 9 with a 4 N sodium hydroxide aqueous solution. The mixture was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-amino-5-benzyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 14f (0.55 g, yield 70%) as a colorless oil.
Workup
- customobtained from the above step at room temperature
- extractionThe mixture was extracted with ethyl acetate
- dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-d4e883143cfc4ed0bd2d22b092ea33cc
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304411B2
Reaction notes
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