Diisobutylaluminumhydride → (S,E)-tert-butyl 2-(4-(hydroxymethyl)styryl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 149B (1.0 g, 3.02 mmol) dissolved in dichloromethane (20 mL) and cooled to −78° C. was added diisobutylaluminum hydride (1.0M in dichloromethane, 10.56 mL, 10.56 mmol) dropwise and the resultant solution stirred at −78° C. for 10 minutes, the cooling bath was then removed and after the reaction reached room temperature it was maintained at this temperature for an additional 1 hour. The solution had acetone (1 mL) added then EtOAc added to it and the mixture extracted with aqueous sodium potassium tartrate solution. The organic extract was then dried, filtered, and concentrated to afford 0.9 g (98%) of the title compound.

Provenance & Evidence