Hydrochloric Acid → HCID 68735863, compound

Participants

Reaction Conditions

Reaction Steps

A flask charged with TFA (0.294 ml, 3.82 mmol) was cooled to about 0° C. and treated with NaBH4 (0.0133 g, 0.353 mmol) in small portions. The mixture was stirred for 1 hour. A solution of 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 (0.032 g, 0.0588 mmol) in DCM (0.18 mL) was added slowly over about 15 minutes. The mixture was allowed to warm to about room temperature and stirred overnight. An additional 3 equivalents of NaBH4 was added the reaction was stirred at about room temperature overnight. The reaction was diluted with water, basified with 2N NaOH, and extracted with EtOAc. The combined organics were washed with water, dried over MgSO4, filtered, and concentrated. The crude residue was purified by column chromatography (4% 7 N ammonia in MeOH/DCM) to yield the free base, which was taken up in DCM and acidified with 2N HCl in Et2O. Removal of the solvents afforded ((R)-5-(3-fluorobenzyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]dihydrochloride (0.001 g, 6%). LCMS (APCI+) m/z 429.4 [M+H]+; Rt=3.15 min.

Provenance & Evidence