Formic Acid → HCID 11615192, compound

HRID 1515114Notes

Reaction equation

HRID 1515114 reaction equation
C(O)=O.C(N(CC)CC)C.ClCCl.[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][CH2:18][C:19]2=[O:24]>O>[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][CH2:18][C@@H:19]2[OH:24]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 44184314-Methyl-1-indanone

Product 1

HCID 11615192HCID 11615192, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of formic acid (0.91 mL, 23.9 mmol) and triethylamine (0.29 mL, 21.0 mmol), a dichloromethane (6.0 mL) solution of 4-methylindan-1-one (1.00 g, 6.84 mmol) was added, and chloro[(1S,2S)—N-(p-toluenesulfonyl)-1,2-diphenyl ethanediamine](mesitylene)ruthenium(II) (128 mg, 0.210 mmol) was added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. Water was added to the reaction solution, and the organic matter was extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution and a saturated sodium chloride solution, then dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 75:25 (v/v)), whereby the objective title compound was obtained as a white solid (0.94 g, yield: 93%).

Workup

  1. extractionthe organic matter was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium bicarbonate solution
  3. dry with materiala saturated sodium chloride solution, then dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  6. customwas obtained
  7. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 75:25 (v/v)), whereby the objective title compound

Sources & evidence

ORD record
ord-292eabfc4dea4714b1324360e4b1c310
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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