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Ethanol → Ethyl 2-[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethanesulfonate

HRID 552708
Notes
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Reaction equation

HRID 552708 reaction equation
[Cl: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]([CH:21]=[CH:22][S:23]([O:26][CH2:27][CH3:28])(=[O:25])=[O:24])[O:12]1.C(O)C.[BH4-].[Na+]>O.[Cl-].[NH4+]>[Cl: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][CH2:22][S:23]([O:26][CH2:27][CH3:28])(=[O:24])=[O:25])[O:12]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 86607308Ethyl 2-[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethenesulfonate

Product 1

HCID 86607309Ethyl 2-[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethanesulfonateYield 93.2%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
25 °C

Procedure

Ethyl 2-[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethenesulfonate (10.500 g, 0.024370 mol) was dissolved in ethanol (200 mL, 3 mol) in a 1-necked round-bottom flask. Sodium borohydride (507.1 mg, 0.01340 mol) was added in 2 portions, 10 min apart. The reaction was stirred for a further 15 min at 25° C. The reaction was diluted with water (400 mL) and 5M ammonium chloride in water (50 mL) and was concentrated in vacuo to remove most of the ethanol. The aqueous residue was extracted with methylene chloride (2×250 mL) and the organic phase was concentrated in vacuo to yield crude product (9.83 g).

Workup

  1. concentrationwas concentrated in vacuo
  2. customto remove most of the ethanol
  3. extractionThe aqueous residue was extracted with methylene chloride (2×250 mL)
  4. concentrationthe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-b14f3b50a4ce422d9bd03c406fb043e7
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07951810B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes