Sodium Sulfate → HCID 67182692, compound

HRID 2410451Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22](OCC)=[O:23])=[CH:16][CH:15]=2)=[N:12][CH:13]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][OH:23])=[CH:16][CH:15]=2)=[N:12][CH:13]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a suspension of lithium aluminum hydride (0.424 g) in tetrahydrofuran (20 mL), a solution of the compound obtained from step c above (2 g) in tetrahydrofuran (10 mL) was added at −20° C. The reaction mixture was stirred for 2 hours at 30° C. and a saturated solution of sodium sulphate was added at the same temperature. The reaction mixture was then filtered through a celite pad and the residue was washed with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure. The residue thus obtained was purified by column chromatography over silica gel using 50% ethyl acetate in hexane as eluant to afford the title compound (1.2 g).

Workup

filtrationThe reaction mixture was then filtered through a celite pad
washthe residue was washed with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue thus obtained
customwas purified by column chromatography over silica gel using 50% ethyl acetate in hexane as eluant

Sources & evidence

ORD record: ord-46f8257eacf34c349d3641974516a1cf
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816073B2

Reaction notes

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