Triethylamine → HCID 66838782, compound

Participants

Reaction Steps

The deprotected amine (368 mg, 0.70 mmol) was stirred in dry CH2Cl2 (10 mL) under N2 atmosphere and NEt3 (98 μL, 0.70 mmol) was added to give a clear brown solution. 5-Bromovaleryl chloride (140 μL, 1.05 mmol, 1.5. equiv.) was added followed by triethylamine (98 μL, 0.70 mmol). The reaction mixture was stirred at rt for 16 h then diluted with CH2Cl2 (1×20 mL) and washed with 1 M aqueous hydrochloric acid (1×20 mL), 1 M aqueous sodium hydroxide (1×20 mL) and saturated brine (1×20 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give a crude yellow chalky solid which was purified by column chromatography on silica (50% ethyl acetate/petroleum ether) to give 29 (153 mg, 48%) as a yellow solid.

Provenance & Evidence