Diisobutylaluminumhydride → HCID 73096807, compound

Participants

Reaction Conditions

Reaction Steps

1-methyl ester and 3-tert-butoxycarbonylamino-2,2-dimethyl-succinic acid dimethyl ester (0.47 g, 1.53 mmol) was dissolved in dichloromethane (3 mL) and cooled to −78° C. Diisobutylaluminum hydride (3.4 mL of a 1M dichloromethane solution, 3.4 mmol) was slowly added. The reaction mixture was warmed to room temperature with stirring over 16 h. Additional diisobutylaluminum hydride (a total of 6.8 mL of a 1M solution, 6.8 mmol) was added portionwise over the next 24 h until thin layer chromatography indicated the starting material was consumed. Aqueous ammonium chloride solution and ethyl acetate were added to the reaction, the layers were separated and the aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with sodium chloride solution and dried over sodium sulfate. After evaporation, the residue was purified by silica gel chromatography (ethyl acetate/hexanes) to give 104 mg (29%) of (3-hydroxy-1-hydroxymethyl-2,2-dimethyl-propyl)-carbamic acid tert-butyl ester.

Provenance & Evidence