[CH2:1]([OH:12])[C@H:2]1[O:8][C:6](=[O:7])[C@H:5]([OH:9])[C@@H:4]([OH:10])[C@@H:3]1[OH:11].[C:13]12(NC)[CH2:19][CH:16]([CH2:17][CH2:18]1)[CH:15]=[CH:14]2.C12(C#N)CC(CC1)C=C2.[H-].[H-].[H-].[H-].[Li+].[Al+3].C[OH:38]>>[O:7]=[C:6]([OH:8])[C@@H:5]([C@H:4]([C@@H:3]([C@@H:2]([CH2:1][OH:12])[OH:38])[OH:11])[OH:10])[OH:9].[CH:13]12[CH2:19][CH:16]([CH2:17][CH2:18]1)[CH:15]=[CH:14]22 ml methanol was added to a 50 ml flask containing 1 g Glucolactone (Aldrich), the solid does not dissolve initially. By the addition of 0.74 g Norbornenyl-methylamine (prepared in lab by the reduction of norbornene carbonitrile with LiAlH4), it disappeared gradually within 20 minutes. The reaction proceeded overnight at room temperature. After the reaction, methanol was removed on a rotary evaporator, and the product was recrystalized from iPrOH/petroleum ether at −4° C. with a yield greater than 70%.
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