반응 #3105

반응 방정식

racemic 1-acetoxyindene

acetone

→

(S)-1-acetoxyindene

수율 44.6%

(R)-inden-1-ol

수율 46.1%

용매

phosphate

반응 조건

후처리

1. 1
   여과The reaction solution was filtered on Celite
2. 2
   기타to remove lipase
3. 3
   추출The liltrate was extracted with diethyl ether
4. 4
   기타the extracted solution was dried on magnesium sulfate
5. 5
   기타The solvent was removed under a reduced pressure

실험 절차

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).

출처