Potassium Bromide → tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate
Reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][OH:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].[O-]Cl.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[C:4]([O:3][C:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH:13]=[O:14])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
To a solution of (R)-Boc-3-pyrrolidinemethanol (5.0 g, 24.8 mmol) in DCM was added TEMPO (80 mg, 0.5 mmol) and potassium bromide (150 mg, 1.3 mmol). This mixture was cooled to 5° C. and vigorously stirred as a pre-chilled (at 0° C.) 1:1 mixture of NaOCl in water (53 mL) and a saturated, aqueous NaHCO3 solution (53 mL) was added dropwise. The resultant mixture was extracted with DCM (3×50 mL). The combined organic layers were washed with water (50 mL) and saturated aqueous NaCl (50 mL). The organic layer was dried over anhydrous Na2SO4 to yield 4.3 g of the title compound, which was used without further purification.
Workup
- temperaturea pre-chilled
- extractionThe resultant mixture was extracted with DCM (3×50 mL)
- washThe combined organic layers were washed with water (50 mL) and saturated aqueous NaCl (50 mL)
- dry with materialThe organic layer was dried over anhydrous Na2SO4
Sources & evidence
- ORD record
- ord-ba8e645b712741dc8de9cfdb935b0ce6
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242164B2
Reaction notes
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