Aminoacetaldehyde dimethyl acetal → Phenylmethyl 2-(2,2-dimethoxyethyl)hydrazinecarboxylate

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Reaction Conditions

Reaction Steps

Aminoacetaldehyde dimethyl acetal (0.430 g, 3.95 mmol) was added to a solution of N-CBZ-3-phenyl-oxaziridine (1.11 g, 4.35 mmol) (prepared as described in Tetrahedron Let. 1993, 6859, the disclosure of which is entirely incorporated herein by reference) in CH2Cl2 (20 mL) at 23° C. The resulting yellow solution was stirred at 23° C. for 18 h, and it then was concentrated under reduced pressure. Purification of the residue by flash column chromatography (3% CH3OH/CH2Cl2) provided 1-CBZ-2-(2,2-dimethoxyethyl)-hydrazine (0.434 g, 43%) as a pale yellow oil: Rf =0.40 (5% CH3OH/CH2Cl2); IR (thin film) 3317, 1721, 1456 cm-1 ; 1H NMR (C6D6) δ 2.96 (bs, 2H), 3.06 (bs, 6H), 3.97 (bs, 1H), 4.37 (bs, 1H), 4.97 (bs, 2H), 5.87 (bs, 1H), 6.98-7.18 (m, 5H).

Provenance & Evidence