Sodium Bicarbonate → HCID 86611031, compound

HRID 2245919Notes

Reaction equation

HRID 2245919 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][C:28]2([C:33](OC)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1.[BH4-].[Li+].C([O-])(O)=O.[Na+]>O1CCCC1>[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:28]2([CH2:33][OH:34])[CH2:29][CH2:30][CH2:31][CH2:32]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 86611027HCID 86611027, compound

Product 1

HCID 86611031HCID 86611031, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(1-methoxycarbonyl-cyclopent-1-yloxy)-benzyl]-benzene (0.15 g) in dry tetrahydrofuran (3 mL) chilled in an ice-bath is added lithium borohydride (8 mg). The reaction mixture is stirred at ambient temperature for 16 h. Aqueous NaHCO3 solution is added and the resulting mixture is extracted with ethyl acetate. The combined organic layers are dried (Na2SO4), the solvent is removed and the residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1).

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. dry with materialThe combined organic layers are dried (Na2SO4)
  3. customthe solvent is removed
  4. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1)

Sources & evidence

ORD record
ord-07b6a907871e4969b777c803d0f0c99e
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

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