Sodium cyanoborohydride → benzyl (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)carbamate

HRID 511609Notes

Reaction equation

HRID 511609 reaction equation
[CH3:1][C:2]1([CH3:23])[O:6][C@@H:5]2[C@@H:7]([CH2:20][NH:21][CH3:22])[O:8][C@@H:9]([N:10]3[CH:18]=[N:17][C:16]4[C:11]3=[N:12][CH:13]=[N:14][C:15]=4[NH2:19])[C@@H:4]2[O:3]1.O=[C:25]1[CH2:28][CH:27]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:26]1.[BH3-]C#N.[Na+]>CO>[CH2:32]([O:31][C:30](=[O:39])[NH:29][CH:27]1[CH2:28][CH:25]([N:21]([CH2:20][C@@H:7]2[C@@H:5]3[C@@H:4]([O:3][C:2]([CH3:23])([CH3:1])[O:6]3)[C@H:9]([N:10]3[CH:18]=[N:17][C:16]4[C:11]3=[N:12][CH:13]=[N:14][C:15]=4[NH2:19])[O:8]2)[CH3:22])[CH2:26]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 110236419-((3aR,4R,6R,6aR)-2,2-Dimethyl-6-((methylamino)methyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amineHCID 19794323Benzyl (3-oxocyclobutyl)carbamate

Product 1

HCID 86666115benzyl (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)carbamateYield 29.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 9-((3aR,4R,6R,6aR)-2,2-dimethyl-6-((methylamino)methyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine (190 mg, 0.59 mmol) and benzyl (3-oxocyclobutyl)carbamate (240 mg, 1.37 mmol) in MeOH (5 mL) was added Ti[OCH(CH3)2]4 (216 mg, 0.59 mmol). The mixture was stirred at rt for 1 h. Then NaCNBH3 (95 mg, 1.52 mmol) was added, the reaction was stirred at rt overnight. The reaction was filtered and evaporated, the residue was purified by prep-TLC (DCM:MeOH=20:1) to obtain the desired compound (90 mg, yield 29%).

Workup

  1. stirringthe reaction was stirred at rt overnight
  2. filtrationThe reaction was filtered
  3. customevaporated
  4. customthe residue was purified by prep-TLC (DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-7ed23fc283d84dee9734e43b3e193e60
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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