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 552708Notes

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

Participants

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

concentrationwas concentrated in vacuo
customto remove most of the ethanol
extractionThe aqueous residue was extracted with methylene chloride (2×250 mL)
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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