Sodium Azide → (2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate
Reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8](OS(C)(=O)=O)[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4].[N-:22]=[N+:23]=[N-:24].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([N:22]=[N+:23]=[N-:24])[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4]Participants
4
Conditions
- Temperature
- 90 °C
Procedure
(2S,4R)-4-Methanesulfonyloxypyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-methyl ester (11.9 g, 37 mmol) and NaN3 (2 equiv) were mixed in DMSO (160 mL) and stirred at 90° C. for 16 hours. The mixture was cooled then partitioned between water (200 mL) and EtOAc (400 mL). The aqueous layer was discarded, the organics washed with water (200 mL) and saturated aqueous NaCl (200 mL), then dried over Na2SO4. The solvent was evaporated to afford the title compound (8.5 g, 31 mmol), which was used without further purification. MS m/z: [M+H]+ calcd for C11H18N4O4, 270.3. found 271.3.
Workup
- temperatureThe mixture was cooled
- customthen partitioned between water (200 mL) and EtOAc (400 mL)
- washthe organics washed with water (200 mL) and saturated aqueous NaCl (200 mL)
- dry with materialdried over Na2SO4
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-50dd886b58bc4cf3b5714c8a7f205117
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106082B2
Reaction notes
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