Water → (S)-tert-butyl 3-formylpyrrolidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].[O-]Cl.[Na+].O.C([O-])(O)=O.[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)-3-hydroxymethylpyrrolidine-1-carboxylic acid t-butyl ester (7.4 g, 37 mmol) in DCM (74 mL, 1.2 mol) was added TEMPO (100 mg, 0.7 mmol) and potassium bromide (200 mg, 2 mmol). This mixture was cooled to 0° C. and vigorously stirred as a pre-chilled (at 0° C.) 1:1 mixture of 0.7 M of NaOCl in water (78 mL, 55 mmol) and a saturated, aqueous NaHCO3 solution (75 mL) was added dropwise over a period of 10 minutes. The resultant mixture was extracted with DCM (3×100 mL). The combined organic layers were washed with water (2×100 mL), then saturated aqueous NaCl (1×100 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to yield the title compound, which was used without further purification (5.8 g).
Workup
- temperaturea pre-chilled
- extractionThe resultant mixture was extracted with DCM (3×100 mL)
- washThe combined organic layers were washed with water (2×100 mL)
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-29447da4127847ea867a4387b8bee369
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933249B2
Reaction notes
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