2-Cyclopentyl-4-(4-methylpent-1-ynyl)-5-nitrophenyl methyl carbonate → 5-Amino-2-cyclopentyl-4-(4-methylpent-1-ynyl)phenyl methyl carbonate

Participants

Reaction Steps

2-Cyclopentyl-4-(4-methylpent-1-ynyl)-5-nitrophenyl methyl carbonate (75 mg, 0.22 mmol) was dissolved in a mixture of glacial acetic acid (940 μL) and water (235 μL). Zn dust (71 mg, 1.09 mmol) was added at room temperature and the reaction stirred for 10 min. The reaction was diluted with methanol (5 mL), filtered and concentrated. The product was brought up in dichloromethane, washed with 50% saturated NaHCO3, dried over Na2SO4, filtered, and dried down to provide 5-amino-2-cyclopentyl-4-(4-methylpent-1-ynyl)phenyl methyl carbonate as a clear orange oil (68 mg, 99% yield). LC/MS m/z 316.2 [M+H]+.

Provenance & Evidence