Formaldehyde → HCID 135797755, compound

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Reaction Steps

Dissolve the free base obtained from Example 609 (0.078 g, 0.16 mmol) in dichloromethane (8 ml). Add sodium triacetoxyborohydride (0.066 g, 0.31 mmol) and formaldehyde (0.005 g, 0.16 mmol, 0.013 g of a 37% aqueous solution) and stir the mixture for two hours at ambient temperature. Dilute the mixture with saturated aqueous sodium chloride (50 mL) and extract three times with dichloromethane. Combine the organic layers, dryover sodium sulfate and remove the solvent under reduced pressure. Purification via flash chromatography, eluting with a linear gradient starting with 100% of a stock mixture of 80% dichloromethane with 20% hexanes and going to 85% of the stock mixture with 15% 2M ammonia in methanol, gives the free base of the title compound (0.062 g, 0.12 mmol, 77% yield) as a yellow amorphous solid. It is then converted to the succinate salt as described previously: Mass Spectrum (m/e): 513(M+1); Exact Mass Spec: Calc. 513.2278; Found 513.2284.

Provenance & Evidence