Diisopropylamine → 1-(3-Nitrobenzoyl)pyrrolidine
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.OC1C2N=NNC=2C=CC=1.CNC(N=C=NCC)CCNC.C(NC(C)C)(C)C>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:9])([O-:3])=[O:2]Participants
Procedure
To a solution of 1.98 g of meta-nitrobenzoic acid in 50 mL of dichloromethane are successively added under argon, at 0° C., 0.81 mL of pyrrolidine, 0.13 g of hydroxybenzotriazole, 2.3 g of 1,3-dimethylaminopropyl-3-ethyl carbodiimide and 3.43 mL of diisopropylamine. The reaction mixture is then stirred at room temperature for 15 hours and then washed with water. The organic phase is then washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of ethyl acetate and cyclohexane (60/40 by volume) to give 1.92 g of 1-(3-nitrobenzoyl)pyrrolidine, the characteristics of which are as follows:
Workup
- washwashed with water
- washThe organic phase is then washed with saturated sodium chloride solution
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue is purified by chromatography on a column of silica
- washeluting with a mixture of ethyl acetate and cyclohexane (60/40 by volume)
Sources & evidence
- ORD record
- ord-be54134fcddc4232a145f69ec72a556a
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935819B2
Reaction notes
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