Reaction #7117

Reaction equation

Thionyl chloride

cis-2-aminocyclohexanecarboxylic acid

methanol

→

cis-2-aminocyclohexanecarboxylic acid methyl ester

Conditions

Workup

1. 1
   OtherThe clear solution was then evaporated to dryness
2. 2
   Otherthe residual volatiles were removed on high vacuum

Procedure

Thionyl chloride (5.48 g, 46.1 mmol) was added dropwise to a solution of cis-2-aminocyclohexanecarboxylic acid (2.0 g, 14.0 mmol) in methanol (50 mL) at 0° C. The mixture was allowed to warm to room temperature and stir for 18 h. The clear solution was then evaporated to dryness, and the residual volatiles were removed on high vacuum. The crude product, cis-2-aminocyclohexanecarboxylic acid methyl ester, was isolated in quantitative yield and used in the next reaction without purification: 1H NMR (400 MHz, CDCl3) δ 8.50 (s br, 2 H), 3.78 (s, 3 H), 3.59 (s br, 1 H), 3.18 (s br, 1 H), 2.27 (m, 1 H), 2.08 (m, 1 H), 1.88 (m, 2 H), 1.45 (m, 4 H).

Source