tert-Butanol → HCID 406593, compound

HRID 864997Notes

Reaction equation

HRID 864997 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

5

Reactant 3

HCID 6386tert-ButanolHCID 4148881Lithium borohydrideHCID 19027594HCID 19027594, compound

Product 1

HCID 406593HCID 406593, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. additionwas added in portions
  2. stirringstirring
  3. waitwas continued over night
  4. filtrationInorganic material was filtered off
  5. washwashed with tert. butanol
  6. customthe filtrate evaporated to small volume

Sources & evidence

ORD record
ord-50c4c685d05b4d138fe6e4647b50de1c
Source dataset
uspto-grants-1996_10
Patent number
US05565461

Reaction notes

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