Reaktion #3105

Reaktionsgleichung

racemic 1-acetoxyindene

acetone

→

(S)-1-acetoxyindene

Ausbeute 44.6%

(R)-inden-1-ol

Ausbeute 46.1%

Lösungsmittel

phosphate

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction solution was filtered on Celite
2. 2
   Sonstigeto remove lipase
3. 3
   ExtraktionThe liltrate was extracted with diethyl ether
4. 4
   Sonstigethe extracted solution was dried on magnesium sulfate
5. 5
   SonstigeThe solvent was removed under a reduced pressure

Vorschrift

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).

Quelle