7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine → 5,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehyde

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Reaction Steps

8-2 (10 g, 0.048 mol) was treated with trifluoroacetic acid (50 mL) and the resulting solution stirred under argon for 12.5 h. The TFA was removed at reduced pressure and the residue partitioned between sat. NaHCO3 and CH2Cl2. The organic layer was dried, concentrated and passed through a 3 in. pad of silica gel (10% acetone/CH2Cl2) and concentrated to afford 8-3 as a yellow crystalline solid.

Provenance & Evidence