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].CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].Cl[O-].[Na+].O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[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
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)-3-hydroxymethyl-pyrrolidine-1-carboxylic acid t-butyl ester (21.6 g, 107 mmol, 1.0 eq.) in DCM (220 mL), was added TEMPO (300 mg, 2 mmol, 0.02 eq.) and potassium bromide (600 mg, 5 mmol, 0.05 eq.) This mixture was cooled at 0° C. and a prechilled (at 0° C.) 1:1 mixture of 0.7 M of sodium hypochlorite in water (230 mL, 1.5 eq.) and saturated, aqueous NaHCO3 (230 ml) was added drop-wise over a period of 90 minutes. The resultant mixture was extracted with DCM (3×100 mL). The combined organic layers were washed with water (2×100 mL), and then saturated aqueous NaCl (1×100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield (S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester (14.6 g).
Workup
- 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 sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7c260368093841a5a13e7aa3a07e7c91
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729119B2
Reaction notes
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