Potassium Sodium Tartrate → HCID 57771484, compound

HRID 2070597Notes

Reaction equation

HRID 2070597 reaction equation
C[O:2][C:3]([C:5]1[CH2:32][CH2:31][CH2:30][C@@:7]2([CH2:11][C@H:10]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[CH:6]=1)=O.[H-].COCCO[Al+]OCCOC.[Na+].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[Si:13]([O:12][C@@H:10]1[CH2:9][CH2:8][C@:7]2([CH2:30][CH2:31][CH2:32][C:5]([CH2:3][OH:2])=[CH:6]2)[CH2:11]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 57771620HCID 57771620, compound

Product 1

HCID 57771484HCID 57771484, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2R,5R)-2-(tert-butyldiphenylsilanyloxy)-spiro[4.5]dec-6-en e-7-carboxylic acid methyl ester (615 mg) obtained in Step 6 in toluene (7 mL) was added dropwise sodium bis(2-methoxyethoxy)aluminum hydride (65% toluene solution; 486 mg) under ice-cooling, followed by stirring the mixture under ice-cooling for 0.5 hour. To the reaction mixture was added dropwise 1M aqueous Rochelle salt solution (10 mL), followed by stirring at room temperature for 2 hours, and the reaction mixture was extracted with toluene. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:6 to 1:5) to give [(2R,5R)-2-(tert-butyldiphenylsilanyloxy)-spiro[4.5]dec-6-en-7-yl]-methanol (539 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 0.5 hour
  3. stirringby stirring at room temperature for 2 hours
  4. extractionthe reaction mixture was extracted with toluene
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:6 to 1:5)

Sources & evidence

ORD record
ord-41dd315be6e9404ba140e19ac45aa0a0
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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