Acetic Acid → HCID 44252387, compound

A solution of the title compound from Example 33 (1.40 g, 4.16 mmol) and formalin (5.8 mL, 37% aqueous solution) in acetonitrile (40 mL) was mixed in portions with sodium cyanoboron hydride (1.03 g, 16.6 mmol) and stirred for 45 min at room temperature. Concentrated acetic acid was then added until a neutral reaction occurred and the mixture stirred for 45 min at room temperature. For work up the solvent was removed in a vacuum, the residue taken up in 2N NaOH (40 mL) and then extracted with ether (3×40 mL). The organic phase was dried over Na2SO4, filtered and concentrated to low volume in a vacuum. The remaining residue was purified by flash chromatography with ethyl acetate (methanol→methanol+2% TEA).

1. stirringthe mixture stirred for 45 min at room temperature
2. customFor work up the solvent was removed in a vacuum
3. extractionextracted with ether (3×40 mL)
4. dry with materialThe organic phase was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated to low volume in a vacuum
7. customThe remaining residue was purified by flash chromatography with ethyl acetate (methanol→methanol+2% TEA)

ORD record

ord-7399425ebb24445fa510b992e11ae566

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403767B2