Reaction #1583897

Reaction equation

D-Leucine

HBr

sodium nitrite

→

Intermediate ( 9a )

Yield 86.0%

(R)-2-Bromo-4-methylpentanoic acid

Yield 86.0%

Solvents

water

water

Conditions

Workup

1. 1
   Extractionextracted twice with EtOAc
2. 2
   Washwashed twice with saturated aqueous NaCl
3. 3
   Dryingdried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Procedure

D-Leucine (9.9 g, 75.2 mmol) was dissolved in 3M HBr in water (120 mL) and cooled to 0° C. A solution of sodium nitrite (8.3 g, 120 mmol) in water (20 mL, 100 mmol) was added. The mixture was stirred at 0° C. for 2.5 hours, extracted twice with EtOAc, washed twice with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated to afford 12.6 g (86%) of Intermediate (9a) as a pale yellow oil. This was taken on to the next step without further purification.

Source