N-Benzyl trans-4,5-bis(hydroxymethyl)isoxazolidine → (+/-)-3-[(Benzylamino)methyl]butane-1,2,4-triol

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Reaction Steps

Zinc dust (0.47 g, 7.2 mmol) was added to a solution of N-benzyl trans-4,5-bis(hydroxymethyl)isoxazolidine (0.32 g, 1.43 mmol) in acetic acid (6 ml) and the mixture stirred vigorously for 1.5 hrs after which time the starting material had been consumed. The mixture was filtered through a plug of celite and the filtrate concentrated to dryness before being redissolved in DCM, preabsorbed onto silica and then fractionated by chromatography, eluting isocratically with M/7M NH3-MeOH, (4:1) to give the aminotriol (0.26 g, 81%) as an immobile syrup. 1H NMR (CDCl3) δ 3.90 (q, J=4.0 Hz, 1H), 3.80 (s, 2H), 3.75 (d, J=5.1 Hz, 2H), 3.66 (dq, J=11.7, 3.9 Hz, 2H), 2.94 (d, J=6.9 Hz, 2H), 1.78 (m, 1H). 13C NMR 138.9, 129.1, 128.7, 127.9, 73.7, 65.4, 65.3, 54.4, 48.9, 43.9. −ESMS—clean spectrum shows only MH+ (226) and MNa+ (248), C12H19NO3.

Provenance & Evidence