Triethylamine → 2-Dimethylcarbamoyl-5-methyl-hexahydro-cyclopenta[c]pyrrole-5-carbonylazide
Reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH3:16])([C:13](O)=[O:14])[CH2:12][CH:7]2[CH2:6]1)=[O:4].C(N(CC)CC)C.ClC(OCC)=O.[N-:31]=[N+:32]=[N-:33].[Na+]>CC(C)=O.O>[CH3:1][N:2]([CH3:17])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH3:16])([C:13]([N:31]=[N+:32]=[N-:33])=[O:14])[CH2:12][CH:7]2[CH2:6]1)=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Upon cooling by an ice-water bath, 2-dimethylcarbamoyl-5-methyl-octahydro-cyclopenta[c]pyrrole-5-carboxylic acid 12c (1.0 g, 4.2 mmol) was dissolved in 25 mL of acetone with stirring, followed by dropwise addition of a solution of triethylamine (463.5 mg, 4.58 mmol) and ethyl chloroformate (497 mg, 4.58 mmol) in 10 mL of acetone at −5° C. The reaction mixture was reacted for 15 minutes at −5° C. followed by addition of a solution of sodium azide (546 mg, 8.4 mmol) in 10 mL of water. Then the reaction mixture was stirred for another 30 minutes at −5° C., and quenched with 25 mL of water and extracted with ethyl acetate (50 mL×3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound 2-dimethylcarbamoyl-5-methyl-hexahydro-cyclopenta[c]pyrrole-5-carbonylazide 12d (700 mg) as a yellow oil.
Workup
- temperatureUpon cooling by an ice-water bath
- customThe reaction mixture was reacted for 15 minutes at −5° C.
- stirringThen the reaction mixture was stirred for another 30 minutes at −5° C.
- customquenched with 25 mL of water
- extractionextracted with ethyl acetate (50 mL×3)
- dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b852e3cb776345d893eebebc28ce89aa
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415349B2
Reaction notes
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