Réaction #3105

Équation de réaction

racemic 1-acetoxyindene

acetone

→

(S)-1-acetoxyindene

Rendement 44.6%

(R)-inden-1-ol

Rendement 46.1%

Solvants

phosphate

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction solution was filtered on Celite
2. 2
   Autreto remove lipase
3. 3
   ExtractionThe liltrate was extracted with diethyl ether
4. 4
   Autrethe extracted solution was dried on magnesium sulfate
5. 5
   AutreThe solvent was removed under a reduced pressure

Mode opératoire

1.0 g (5.75 mmol) of racemic 1-acetoxyindene and 57.5 mg of lipase PS (made by Amano Seiyaku Sha, derived from Pseudomonas bacterium) were suspended in 58 ml of phosphate buffer (0.1M)-acetone mixed solution (9:1 V/V) and stirred at 37° C. for 48 hours. The reaction solution was filtered on Celite to remove lipase. The liltrate was extracted with diethyl ether and the extracted solution was dried on magnesium sulfate. The solvent was removed under a reduced pressure and the residue was subjected to silica gel column chromatography (eluate:ethyl acetate-hexane, 1:10 V/V) to separate into 446 mg (yield 44.6%) of (S)-1-acetoxyindene and 350 mg (yield 46.1%) of (R)-inden-1-ol respectively. The specific rotations and optical purities thereof were as shown below. The optical purities were determined by high speed liquid chromatography (column: chiral cell OD, eluate: isopropanol-hexane, 1% V/V).

Source