tert-Butanol → HCID 406593, compound

Reaction equation

[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([CH2:11][CH:12]([CH2:17][C:18](OC)=[O:19])[C:13](OC)=[O:14])[CH:6]=[N:7]2)=[N:3][CH:2]=1.C(O)(C)(C)C.[BH4-].[Li+]>O>[OH:19][CH2:18][CH2:17][CH:12]([CH2:13][OH:14])[CH2:11][N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10]

Participants

Procedure

Dimethyl 2-(adenine-9-ylmethyl)succinate (2.93 g, 0.010 mol) was dissolved by warming with tert. butanol (120 ml), lithium borohydride (1.10 g, 0.05 mol) was added in portions and the mixture was stirred at ambient temperature for 3 h, water (10 ml) was added and stirring was continued over night. Inorganic material was filtered off and washed with tert. butanol and the filtrate evaporated to small volume. Chromatography on silica (ethyl acetate+methanol+water 7+2+1) afforded pure 9-(4-hydroxy-2-hydroxymethylbutyl)adenine.