Ethyl Acetate → [4-((S)-3-Hydroxy-cyclopentyl)-phenyl]-carbamic acid benzyl ester

Participants

Reaction Steps

[4-((S)-3-Oxo-cyclopentyl)-phenyl]-carbamic acid benzyl ester (150 mg, 0.5 mmol) was dissolved in EtOH (1 mL) and EtOAc (0.1 mL) to form a clear solution. To this solution was added powder NaBH4 (50 mg) with stirring. The reaction was judged to be complete by TLC (30% EtOAc in heptane). The reaction was quenched by EtOAc (2 mL) and NaHCO3 aq. solution (2 mL). The two layers were separated and the aqueous layer was extracted with EtOAc (2×2 mL). The combined extracts were washed with NaHCO3 aq. (2 mL), brine (2 mL), and dried (K2CO3). The solution was filtered through a silica gel pad, eluted with EtOAc. The filtrate was concentrated to dryness to afford 155 mg (100%) of the title compound as a very white crystalline material. mp 99.0-100.6° C.

Provenance & Evidence