HCID 86611030, compound → HCID 86611029, compound

HRID 2245918Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]2[CH2:32][CH2:31][CH2:30][C:29]2=[O:33])=[CH:23][CH:22]=1>O1CCCC1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C@@H:28]2[CH2:32][CH2:31][CH2:30][C@@H:29]2[OH:33])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(2-oxo-cyclopent-1-yloxy)-benzyl]-benzene (0.10 g) in dry tetrahydrofuran (3 mL) chilled to −78° C. is added L-selelctride (1 mol/l in tetrahydrofuran, 0.33 mL). The resulting solution is stirred at −78° C. for 2 h, then diluted with dichloromethane and quenched with aqueous hydrochloric acid (1 mol/l). The organic layer is separated and the aqueous phase is extracted with dichloromethane. The combined organic layers are dried (Na2SO4), the solvent is removed in vacuo and the residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1).

Workup

customquenched with aqueous hydrochloric acid (1 mol/l)
customThe organic layer is separated
extractionthe aqueous phase is extracted with dichloromethane
dry with materialThe combined organic layers are dried (Na2SO4)
customthe solvent is removed in vacuo
customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1)

Sources & evidence

ORD record: ord-2f9fe6d1c12b4d57b5be11d7abe609e2
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683160B2

Reaction notes

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