Sodium Sulfate → HCID 67182692, compound

HRID 84041Notes

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-25c3e500eb804546995694f3737c1427
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846910B2

Reaction notes

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