Sodium Bromide → tert-butyl (2S,5S)-2-formyl-5-methylpyrrolidine-1-carboxylate
Reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][C@H:5]([CH3:8])[N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[Br-].[Na+].C(=O)(O)[O-].[Na+].Cl[O-].[Na+]>ClCCl.CC1(C)N([O])C(C)(C)CCC1>[CH:2]([C@@H:3]1[CH2:7][CH2:6][C@H:5]([CH3:8])[N:4]1[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])=[O:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (2S,55)-tert-butyl 2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate (5.15 g, 23.9 mmol) in dichloromethane, was added TEMPO (0.075 g, 0.48 mmol), sodium bromide (0.246 g, 2.39 mmol) and sodium bicarbonate (0.442 g, 5.26 mmol). Sodium hypochlorite (2.67 g, 35.9 mmol) of a 6% solution was added and the biphasic mixture was vigorously stirred for 2 hours at room temperature. The reaction mixture was extracted two times with dichloromethane (2×100 mL). The organic layers were combined and washed with saturated sodium thiosulfate solution, dried with sodium sulfate and the solvent was removed in vacuo to yield (2S,5S)-tert-butyl 2-formyl-5-methylpyrrolidine-1-carboxylate (3.9 g, 18.29 mmol, 77%) as a slight colored oil and was used directly in the following step.
Workup
- extractionThe reaction mixture was extracted two times with dichloromethane (2×100 mL)
- washwashed with saturated sodium thiosulfate solution
- dry with materialdried with sodium sulfate
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-aad6e749b4564541b3b301ee0a257ac1
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940718B2
Reaction notes
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