Reaction #7116

Reaction equation

(1S,2R)-2-aminocyclohexanecarboxylic acid

methanol

Thionyl chloride

→

(1S,2R)-2-aminocyclohexanecarboxylic acid methyl ester

Conditions

Workup

1. 1
   Temperaturea chilled
2. 2
   workup.ADDITIONAfter complete addition
3. 3
   Otherthe cold bath was removed
4. 4
   Otherthe reaction mixture was evaporated to dryness under a stream of dry nitrogen

Procedure

Thionyl chloride (4.73 mL, 64.8 mmol) was slowly added to a chilled (ice-water bath) suspension of (1S,2R)-2-aminocyclohexanecarboxylic acid (16.2 mmol) in anhydrous methanol (200 mL). After complete addition, the cold bath was removed and the resulting mixture warmed to room temperature. After 24 h, the reaction mixture was evaporated to dryness under a stream of dry nitrogen. The crude product, (1S,2R)-2-aminocyclohexanecarboxylic acid methyl ester, was obtained as a white solid and used in the next step without purification or characterization.

Source