Sodium cyanoborohydride → N-(7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-O-methyl-hydroxylamine

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Reaction Conditions

Reaction Steps

To a stirred solution of crude 7-chloro-3,4-dihydro-2H-naphthalen-1-one-O-methyl-oxime (5.9 g; 28.14 mmol) prepared as described in example P1a in acetic acid (100 ml) was added portion wise sodium cyanoborohydride 95% (3.54 g; 56.3 mmol) at 15° C. The mixture was stirred for 6 hours at 23° C. Most of acetic acid was removed under reduced pressure. The residue was poured in 2N NaOH (100 ml) and was extracted with ethylacetate (3×80 ml). Combined organics were dried over sodium sulfate and solvent was removed in vacuo. The crude (8.2 g) was subject to flash chromatography (eluant: c-hexane/ethyl acetate 90:10) to afford 2.70 g (45% of theory) of N-(7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-O-methyl-hydroxylamine as a yellow oil.

Provenance & Evidence