反应详情

A solution of [(S)-5-benzyloxycarbonylamino-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-pentyl]-carbamic acid tert-butyl ester (0.63 g, 1.27 mmol) in DCM (5.1 ml) and EtOH (5.1 ml) is treated with hydrazine hydrate (0.318 g, 6.35 mmol) and the reaction mixture is stirred at room temperature overnight. A white precipitate forms which is removed by filtration and washed with DCM (3×10 ml). The filtrate is concentrated in vacuo and redissolved in DCM (15 ml) and MeOH (2 ml). Undissolved material is removed by filtration and the filtrate is concentrated in vacuo. The resulting oily yellow solid is purified by chromatography on silica eluting with 10-50% MeOH in DCM (1% TEA) to afford ((S)-1-Aminomethyl-5-benzyloxycarbonylamino-pentyl)-carbamic acid tert-butyl ester as a clear oil; [M+H]+ 366

1. customA white precipitate forms which is removed by filtration
2. washwashed with DCM (3×10 ml)
3. concentrationThe filtrate is concentrated in vacuo
4. dissolutionredissolved in DCM (15 ml)
5. customUndissolved material is removed by filtration
6. concentrationthe filtrate is concentrated in vacuo
7. customThe resulting oily yellow solid is purified by chromatography on silica eluting with 10-50% MeOH in DCM (1% TEA)