[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].[Br-].[Na+].Cl[O-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CC1(C)N([O])C(C)(C)CCC1>[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]A solution of (R)-3-hydroxymethyl-pyrrolidine-1-carboxylic acid t-butyl ester (50.0 g, 248.4 mmol, 1.0 eq.) in DCM (883 mL) was combined with TEMPO (1.9 g, 12.4 mmol, 0.05 eq.) and sodium bromide (2.6 g, 24.8 mmol, 0.1 eq.). The solution was cooled to 0° C. A solution of sodium hypochlorite (272.1 mL, 1.5 eq.) and sodium bicarbonate (31.2 g, 1.5 eq.) was added. Upon completion of the reaction, the mixture was extracted with DCM (3×200 mL) and dried over Na2SO4, to yield (R)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester (50 g).
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