Hydrochloric Acid → HCID 19390049, compound

HRID 1757228Notes

Reaction equation

HRID 1757228 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:9][CH2:8][C:7]2([CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH2:6][CH2:5]1.Cl>C(O)C>[OH:15][CH:12]1[CH2:11][CH2:10][C:7]2([CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15425715HCID 15425715, compound

Product 1

HCID 19390049HCID 19390049, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.400 g) was added in portions to a solution of 10.0 g of 3,9-dioxo-spiro[5.5]undecane (III) (Rice L. M. et al., J.Org.Chem., 1967, 32, 1966) in 80 ml of ethanol, under nitrogen atmosphere, at room temperature. After 1.5 hrs, 10.0 ml. of 1N hydrochloric acid were added and the resulting mixture was evaporated under reduced pressure. The crude residue, dissolved in 150 ml. of ethyl acetate, was washed with water to neutrality. The organic layer, dried over anhydrous sodium sulfate, was evaporated to dryness under reduced pressure to give a mixture of starting material, 3,9-dihydroxy- and 9-hydroxy-3-oxo-spiro[5.5]undecane. The components of the mixture were separated by flash chromatography (SiO2 ; ethyl acetate/n-hexane 70/30) and 2.80 g of 9-hydroxy-3-oxo-spiro[5.5]undecane were obtained as a white solid, mp 65°-67° C. TLC: Rf=0.32 (SiO2 plates, diethylether) 1H-NMR (300 MHz, CDCl3, ppm from TMS): 3.75 (1H, hept), 2.35 (4H, q), 1.25-1.95 (12H, m)

Workup

  1. customthe resulting mixture was evaporated under reduced pressure
  2. dissolutionThe crude residue, dissolved in 150 ml
  3. washof ethyl acetate, was washed with water to neutrality
  4. dry with materialThe organic layer, dried over anhydrous sodium sulfate
  5. customwas evaporated to dryness under reduced pressure
  6. customto give
  7. customThe components of the mixture were separated by flash chromatography (SiO2 ; ethyl acetate/n-hexane 70/30)

Sources & evidence

ORD record
ord-0207d12ab7eb45c68434648042ed41ba
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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