Sodium cyanoborohydride → HCID 23519155, compound

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Reduction of 4-(methoxyimino-methyl)-benzoic acid tert-butyl ester with sodium cyanoborohydride as described in the preparation of compound 1-B gave the title hydroxylamine as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8:2) (56% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.59 (9H, s, t-Bu), 3.49 (3H, s, OCH3), 4.09 (2H, s, NCH2), 7.41 (2H, d, J=8.6 Hz, aromatics), 7.96 (2H, d, J=8.6 Hz, aromatics). The hydrochloride salt was obtained as a white solid: mp 130-132° C. Anal. calcd for C13H19NO3—HCl: C, 57.04; H, 7.36; N, 5.12. Found: C, 56.90; H, 7.27; N, 5.00.

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