Water → (3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)methanol

HRID 511582Notes

Reaction equation

HRID 511582 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][N:22]([CH3:31])[CH:23]2[CH2:26][CH:25]([C:27](OC)=[O:28])[CH2:24]2)[O:12]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:19])([CH3:20])[O:18][C@@H:14]2[C@@H:13]([CH2:21][N:22]([CH3:31])[CH:23]2[CH2:24][CH:25]([CH2:27][OH:28])[CH2:26]2)[O:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67774297methyl3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutanecarboxylate

Product 1

HCID 67777452(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutanecarboxylate (1.0 g, 2.31 mmol) in THF (40 ml) was added LiAlH4 (0.53 g, 13.89 mmol) at 0° C. and the mixture was stirred overnight. Water (1.0 g) and 15% NaOH solution (3.0 g) were added slowly to the mixture and upon stirring for 15 min, the mixture was filtered. The filtrate was concentrated to obtain the crude title compound which was used directly in the next step.

Workup

  1. stirringupon stirring for 15 min
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7d2870d077134100a4544cde83585fb6
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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