Trifluoroacetic acid → HCID 57771543, compound

HRID 2070595Notes

Reaction equation

HRID 2070595 reaction equation
[CH3:1][O:2][C:3]([CH: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)[C:6]1=[O:33])=[O:4].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:32][CH2:31][CH2:30][C@@:7]2([CH2:11][C@H:10]([O:12][Si:13]([C:26]([CH3:29])([CH3:27])[CH3:28])([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:9][CH2:8]2)[CH:6]1[OH:33])=[O:4]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 57771554HCID 57771554, compound

Product 1

HCID 57771543HCID 57771543, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of the crude (2R,5R)-2-(tert-butyldiphenylsilanyloxy)-6-oxo-spiro[4.5]de cane-7-carboxylic acid methyl ester (1.65 g) obtained in Step 4 in toluene (1.6 mL) were added trifluoroacetic acid (5 mL) and triethylsilane (0.52 mL) under ice-cooling, followed by stirring the mixture under ice-cooling for 3 hours. Then, to the reaction mixture was added dropwise a solution of potassium carbonate (4.95 g) in water (20 mL), and the mixture was stirred under ice-cooling for 10 minutes, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated to give (2R,5R)-2-(tert-butyldiphenylsilanyloxy)-6-hydroxy-spiro[4.5]decane-7-carboxylic acid methyl ester (1.76 g) as a crude product.

Workup

  1. temperaturecooling
  2. temperaturecooling for 3 hours
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 10 minutes
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a763d4c5fc1847109874d152fa582101
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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