Hydrochloric Acid → 5-Amino-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide
Reaction equation
[CH3:1][N:2]([CH3:16])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([N+:14]#[C-])([CH3:13])[CH2:12][CH:7]2[CH2:6]1)=[O:4].Cl>C(O)C>[CH3:16][N:2]([CH3:1])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([NH2:14])([CH3:13])[CH2:12][CH:7]2[CH2:6]1)=[O:4]Participants
Procedure
To a solution of 5-isocyano-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 11b (0.388 g, 1.75 mmol) in 15 mL of ethanol was added 0.38 mL of hydrochloric acid (6 N) upon cooling by an ice-water bath. The reaction mixture was warmed up to room temperature and stirred for 1.5 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was quenched with 20 mL of saturated aqueous sodium carbonate. The mixture was extracted with dichloromethane (50 mL×3). The combined organic extracts were evaporated to dryness. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-amino-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 11c (0.28 g, yield 75.7%) as a yellow oil.
Workup
- temperatureupon cooling by an ice-water bath
- customThe mixture was quenched with 20 mL of saturated aqueous sodium carbonate
- extractionThe mixture was extracted with dichloromethane (50 mL×3)
- customThe combined organic extracts were evaporated to dryness
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-4b52407effe449379d974d70f5e2dbce
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304411B2
Reaction notes
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