Sodium borohydride → HCID 59394973, compound

Participants

Reaction Steps

To a solution of 4-chloro-2-cyclopentyl-5-nitrophenyl methyl carbonate (870 mg, 2.90 mmol) and NiCl2 (376 mg, 2.90 mmol) in methanol (10 mL) at 0° C. was added NaBH4 (330 mg, 8.71 mmol) portion-wise. After 10 min the reaction was quenched with NaHCO3 and diluted with ethyl acetate. The reaction mixture was filtered through a pad of Celite and the layers were separated. The aqueous layer was re-extracted with ethyl acetate (3×100 mL) and the combined organic extracts dried over MgSO4. The solution was filtered and concentrated in vacuo to provide 5-amino-4-chloro-2-cyclopentylphenyl methyl carbonate which was used for the next step without further purification (400 mg, 51% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.11 (s, 1H), 6.57 (d, J=11.4 Hz, 1H), 5.38 (s, 1H), 3.85-3.80 (m, 3H), 2.89-2.80 (m, 2H), 1.88-1.81 (m, 2H), 1.75-1.56 (m, 2H), 1.52 (s, 2H), 1.46-1.37 (m, 2H).

Provenance & Evidence