Potassium sodium tartarate → HCID 72388329, compound

HRID 749628Notes

Reaction equation

HRID 749628 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:12](=[CH:23][C:24]#N)[CH:11]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=[O:45].[Na+].[K+]>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH:9]1[CH2:14][CH:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:12](=[CH:23][CH:24]=[O:45])[CH:11]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 72388323HCID 72388323, compound

Product 1

HCID 72388329HCID 72388329, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of Compound 30 (310 mg, 0.635 mmol, 30a:30b=ca. 1:2) in dry toluene (3 mL) cooled to −78° C. was slowly added diisobutylaluminum hydride (763 μL, 0.763 mmol, 1.0 M solution in toluene), and the mixture was stirred for 1.5 h. Excess reagent was decomposed by adding an aqueous solution of saturated potassium sodium tartrate, thereby quenching reaction, and into the mixture was poured ice water, and then extracted with AcOEt. The organic layer was washed with saturated brine, dried over anhydrous MgSO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography (13 g; 5% AcOEt/hexane) to afford Compound 31 (288.5 mg, 93%) as a mixture of two stereoisomers. The ratio of the stereoisomers constituting the mixture was ca. 1:2. It was impossible to know whether the major product was aS*,2R,6R isomer or aR*,2R,6R isomer.

Workup

  1. customquenching
  2. customreaction
  3. extractionextracted with AcOEt
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (13 g; 5% AcOEt/hexane)

Sources & evidence

ORD record
ord-e94e4ba742ab424985664e3934f924f4
Source dataset
uspto-grants-2008_07
Patent number
US07402688B2

Reaction notes

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