Diisobutylaluminum hydride → 2-Tert-butoxycarbonylamino-4-oxo-butyric acid benzyl ester
Reaction equation
[CH2:1]([O:8][C:9](=[O:26])[CH:10]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][C:12](N(OC)C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH2:1]([O:8][C:9](=[O:26])[CH:10]([NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:11][CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
To 2-tert-butoxycarbonylamino-N-methoxy-N-methyl succinamic acid benzyl ester (0.50 g, 1.36 mmol) in THF (5 mL) at −78° C. was added DIBAL-H (0.233 g, 1.67 mmol) dropwise. The mixture was stirred for 1.5 h and monitored by TLC. When completed the reaction was quenched with 5 mL of saturated solution of Rochell salt (KNaC4H4O6.4H2O) (potassium sodium tartrate) and extracted with EtOAc (2×10 mL). The organic layer was washed with H2O, brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound in quantitative yield (0.40 g).