Sodium Hydroxide → HCID 18963909, compound

Participants

Reaction Steps

To a solution of the above oxime (9 g, 22.28 mmol) in glacial acetic acid (50 ml) and CH2Cl2 (75 ml) is added sodium cyanoborohydride (1.7 g). The solution is stirred for 45 minutes at room temperature and subsequently diluted with H2O (200 ml). The resulting mixture is then neutralized with 5N NaOH and solid NaHCO3. The reaction mixture is extracted with EtOAc (2×200 ml) and the combined organic layers washed with saturated NaCl solution, dried over MgSO4, and concentrated in vacuo to yield 2-(4'-fluoro-4-biphenylylmethyl)-6-[2-(N-hydroxyamino)ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Provenance & Evidence