Ammonium Hydroxide → (5-Aminopentyl)(phenylmethoxy)carbamic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

N-(5-Aminopentyl)-N-(tert-butoxycarbonyl)-O-benzylhydroxylamine (7) was prepared by adding Raney nickel (W-2 grade, 0.98 g) and concentrated NH4OH (1.6 mL) to a solution of (4) (0.57 g, 1.87 mmol) in methanol (9.5 mL) in a 250 mL Parr bottle. The suspension was cooled to 0° C. and ammonia was gently bubbled in for 10 minutes. Hydrogenation was carried out on a Parr shaker for 3.5 hours at 55-58 psi. The catalyst was filtered off (Celite) and the filtrate was concentrated to give 0.61 g crude product. Column chromatography using 5% concentrated NH4OH/CH3OH yielded 0.48 g of (7) (83% yield): NMR δ 1.25-1.72 (m, 17 H), 2.64 (t, 2 H, J=7), 3.39 (t, 2 H, J=7), 4.78 (s, 2 H), 7.31 (s, 5 H). Anal. calcd. for C17H28N2O3 : C, 66.21; H, 9.15; N, 9.08. Found: C, 66.24, H, 9.18; N, 9.05.

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