Triethylamine → (S)-tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)pyrrolidine-1-carboxylate
Reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(Cl)Cl>[CH2:26]([O:25][C:23](=[O:24])[NH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of (S)-tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate (1.5 g, 7.5 mmol) in 25 mL CH2Cl2 was added triethylamine (2.1 mL, 15 mmol) at 0° C., followed by the dropwise addition of benzyl chloroformate (1.58 mL, 11.2 mmol). The reaction was allowed to warm to room temperature and was stirred overnight. The mixture was quenched with water, and the aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated. Purification via silica gel chromatography using 3% MeOH in CH2Cl2 gave benzyl((S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylcarbamate (1.5 g, 60%). LC/MS: m/z: 335.5 (M+H)+ at 3.01 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
Workup
- customThe mixture was quenched with water
- extractionthe aqueous layer was extracted twice with CH2Cl2
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customPurification via silica gel chromatography
Sources & evidence
- ORD record
- ord-aee37378269144a5b36c24514fed2b65
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283354B2
Reaction notes
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