Hydrochloric Acid → HCID 23078200, compound

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Reaction Steps

To a dichloromethane solution (8 mL) of the compound of Example 147 (569 mg), triethylamine (303 μL) was added and the mixture was stirred for 5 min. While the mixture was chilled in an ice bath, Boc2O (358 mg) was added and the mixture was stirred for 1 hour. 4N hydrochloric acid was added to adjust the pH of the mixture to 2 to 1. This was followed by the addition of ethyl acetate and a saturated aqueous solution of sodium chloride to separate the mixture into an organic phase and an aqueous phase. The organic layer was dried over anhydrous sodium sulfate, was concentrated, and was dried in a vacuum pump to give a yellow oil. This product was dissolved in DMF (8 mL). To this solution, potassium carbonate (451 mg) and methyl iodide (135 mL) were added and the mixture was stirred at room temperature for 2 hours. The mixture was then extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate and was concentrated. The residue was purified on a silica gel column chromatography (hexane:ethyl acetate=3:1). While chilled in an ice bath, the resultant oil was dissolved in THF (10 mL). To this solution, lithium tetrahydroborate (40.4 mg) and ethanol (1.5 mL) were added and the mixture was stirred in an ice bath for 10 min and at room temperature for the subsequent 1 hour. Following addition of water, 4N hydrochloric acid was added to adjust the pH of the mixture to 2 to 1. Ethyl acetate and water were added to separate the mixture into an organic phase and an aqueous phase. The organic layer was dried over anhydrous sodium sulfate and was concentrated. The residue was purified on a silica gel column chromatography (hexane:ethyl acetate=1:1). Methanol hydrochloride (4 mL) was added to the resultant oil and the mixture was left overnight at room temperature. Subsequently, the solvent was removed to give the desired product as a colorless amorphous (70.0 mg).

Provenance & Evidence