Reaction #40274

Reaction equation

(R)-2-isobutyl-succinonitrile

(R)-2-isobutyl-succinonitrile

toluene

1,8-diazabicyclo[5.4.0]undec-7-ene

→

racemic 2-isobutyl-succinonitrile

Yield 84.0%

Solvents

Water

Conditions

Workup

1. 1
   Otherrecovered from bioconversion of racemic 2-isobutyl-succinonitrile with NIT-102 C2
2. 2
   Temperaturewas refluxed for 2 h
3. 3
   Extractionthe resulting mixture extracted with ethyl acetate (2×10 mL)
4. 4
   WashThe combined organic extracts were washed sequentially with 5% HCl (20 mL) and saturated aqueous sodium chloride (20 mL)
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under vacuum

Procedure

The racemization of (R)-2-isobutyl-succinonitrile was carried out on material recovered from bioconversion of racemic 2-isobutyl-succinonitrile with NIT-102 C2. A mixture of (R)-2-isobutyl-succinonitrile (1.36 g, 10 mmol, 69% ee), toluene (5 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.076 g, 5 mmol) was refluxed for 2 h. Water (10 mL) was added to the reaction and the resulting mixture extracted with ethyl acetate (2×10 mL). The combined organic extracts were washed sequentially with 5% HCl (20 mL) and saturated aqueous sodium chloride (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to give racemic 2-isobutyl-succinonitrile (1.14 g, 84%). Enantiomeric purity was determined by GC using a Chiraldex™ G-TA column (30 M×0.25 mm ID, 125 micron film thickness).

Source