Reaction #710562

Reaction equation

(1R,3S)-3-aminocyclopentanecarboxylic acid

methanol

thionyl chloride

→

title compound

(1R,3S)-Methyl 3-aminocyclopentanecarboxylate hydrochloride

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   OtherThe resulting clear solution was evaporated
4. 4
   Otherazeotroped with methanol (2×5 mL)
5. 5
   Otherair-dried

Procedure

A suspension of (1R,3S)-3-aminocyclopentanecarboxylic acid (500 mg, 3.8 mmol) in methanol (10 mL) was stirred at 0° C. and thionyl chloride (1.40 mL, 19.3 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The resulting clear solution was evaporated, azeotroped with methanol (2×5 mL), air-dried and the title compound obtained as a white powder (680 mg).

Source