Sodium borohydride → HCID 67061959, compound

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Reaction Steps

To a MeOH (0.09 M) solution of trans-N-[3-bromo-5-(3-fluorobenzoyl)-4-methylbenzyl]-N-cyclopropyl-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidine-carboxamide (1 eq., Example 106) was added sodium borohydride (1.4 eq.). The resulting solution was stirred at RT for 15 h before the volatiles were removed in vacuo. The resulting residue carefully added 10% aq. HCl, followed by 1 N aq. NaOH so that the pH of the final solution is ˜10. After extraction with EtOAc, the combined organic extracts were washed further with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Further purification by way of column chromatography (SiO2, 93:7 (v/v) CH2Cl2:2.0 M NH3 in MeOH) afforded the title compound as a mixture of diastereomers. MS (ESI+, M+H): 584.

Provenance & Evidence