Diisobutylaluminum hydride → (3R)-3-(dibenzylamino)cyclopentanecarbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of (3R)-3-(dibenzylamino)-N-methoxy-N-methylcyclopentanecarboxamide (3.34 g, 9.48 mmol) in THF (70 mL) was cooled to about −78° C., followed by the drop-wise addition of DIBAL-H (1.0 M in hexanes, 9.48 mL, 9.48 mmol). The reaction mixture was stirred at about −78° C. for about 1 h, and was quenched by drop-wise addition of saturated aqueous sodium potassium tartrate. The resulting mixture was stirred at room temperature for about 1 h. The solvent was removed under reduced pressure and the aqueous layer was extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by chromatography on neutral alumina eluting with a gradient of 0-20% EtOAc in heptane to yield (3R)-3-(dibenzylamino)cyclopentanecarbaldehyde (1.63 g, 75%) as a colorless oil: LC/MS (Table 2, Method a) Rt=2.03 min; MS m/z: 294 (M+H)+.

Provenance & Evidence