Sodium sulfate decahydrate → HCID 117840022, compound

HRID 714865Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of lithium aluminium hydride (300 mg) in tetrahydrofuran (20 mL) was added dropwise a solution of ethyl 4-(4-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate (1.0 g) obtained in Step A of Example 151 in tetrahydrofuran (10 mL) at −78° C., and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added sodium sulfate decahydrate, and the mixture was stirred at room temperature for 2 hr. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (330 mg).

Workup

stirringthe mixture was stirred at room temperature for 2 hr
customThe insoluble substance was removed by filtration through Celite
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-7f6056a03d994fdb9e95cfc962631a08
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Reaction notes

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