Sodium borohydride → HCID 69812189, compound

Participants

Reaction Steps

To a stirred solution of (R)-tert-butyl 5-(3-fluorobenzoyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.047 g, 0.087 mmol) in MeOH (0.5 mL) was added NaBH4 (0.0036 g, 0.095 mmol) at about 0° C. The reaction was stirred for 1.5 hours and quenched by the addition of saturated NH4Cl solution. The solvent was evaporated under reduced pressure. The solid was dissolved in water and extracted with EtOAc. The combined extracts were washed with brine, dried MgSO4, filtered and concentrated. The crude residue was purified by column chromatography (1-3% MeOH/DCM) to yield tert-butyl 5-((3-fluorophenyl)(hydroxy)methyl)-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.035 g, 74%). LCMS (APCI+) m/z 545.3 [M+H]+; Rt=4.02 min.

Provenance & Evidence