3,3-Dimethylbutylamine → HCID 18794535, compound

Participants

Reaction Steps

Oxalyl chloride (2M in CH2Cl2, 4.3 mL, 8.6 mmol) was added to a stirring suspension of acid 2 (0.90 g, 4.3 mmol) in toluene (20 mL). DMF (1 drop) was added and the reaction began bubbling. After 2 hours, the reaction was evaporated in vacuo. The residue was dissolved in CH2Cl2 (21 mL) and 3,3-dimethylbutylamine (0.87 g, 1.2 mL, 8.6 mmol) was added. After stirring at ambient temperature for 4 hours, the reaction was transferred to a separatory funnel with CH2Cl2 /H2O. Extraction with CH2Cl2 (3×30 mL) and drying over MgSO4 afforded 1.4 g of product after evaporation of the solvent. Flash chromatography (silica gel, 37 mm dia, 40% EtOAc/hexane) afforded 1.2 g of product. Recrystallization from EtOAc/hexane (10 mL/10 mL) afforded 0.89 g (75%) of pure crystalline title compound.

Provenance & Evidence