Sodium Carbonate → HCID 11553707, compound

Participants

Reaction Steps

To a solution of 3-(1-ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)-1,1,1-trifluoro-2-[(5-isoquinolinylimino) methyl]-2-propanol (Intermediate 18) (185 mg, 0.43 mmol) in glacial acetic acid (5 ml) stirred under nitrogen at room temperature, was added sodium triacetoxyborohydride (276 mg, 1.3 mmol) and the solution was stirred for approximately 4 h. Further sodium triacetoxyborohydride (100 mg, 0.47 mmol) was added and the reaction was stirred for 1 h. The solution was then carefully added to saturated aqueous sodium carbonate and when effervescence had ceased was extracted into ethyl acetate (×2). The combined organic layers were washed successively with saturated aqueous sodium carbonate solution, water and finally brine/water (1:1), passed through a hydrophobic frit and evaporated in vacuo to yield a pale yellow oil. The crude product was purified on a 10 g silica SPE cartridge eluting with a 0-100% dichloromethane in heptane gradient followed by 1% methanol in dichloromethane. This gave, in order of elution, Example 4-D2 (racemic diastereomer 2) (45 mg) and Example 4-D1 (racemic diastereomer 1) (35 mg).

Provenance & Evidence