Hydrochloric Acid → HCID 58248298, compound

Participants

Reaction Steps

To a solution of (2S)-2′-oxo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,1′,2′,3-tetrahydrospiro[cyclopenta[b]quinoline-2,3′-pyrrolo[2,3-b]pyridine]-7-carbaldehyde from Step I (142 mg, 0.320 mmol) in MeOH (17 mL) was introduced gaseous anhydrous hydrogen chloride by bubbling the gas through the solution until the MeOH was saturated and mildly warmed. This saturation with HCl was repeated once again after 3 hours then the sealed reaction was allowed to sit at ambient temperature for 19 hours. The solution was then purged with a stream of nitrogen for 20-30 minutes, before being concentrated in vacuo. MeOH (50 mL) was added, then removed in vacuo, repeating this addition/concentration twice to remove excess HCl. The residue was dissolved in MeOH (17 mL) prior to the addition of concentrated aqueous NH4OH (0.7 mL). After 20 minutes the MeOH was removed in vacuo, fresh MeOH (50 mL) was added then remove in vacuo to produce a residue. This residue was dissolved in water (1.35 mL) plus 4 drops on cone. H2SO4. This aqueous solution was transferred to an Erlenmeyer flask using water (3 mL) and 2 more drops of conc. H2SO4. Slow neutralization with aqueous NaOH (1 M, ˜2.5 mL) provided a solid which was filtered, washed with water, air dried and vacuum dried to give the title compound. MS: m/z=316 (M+1).

Provenance & Evidence