Reaction #7118

Reaction equation

Chlorotrimethylsilane

cis-2-aminocycloheptanecarboxylic acid

→

cis-2-aminocycloheptanecarboxylic acid methyl ester

Yield 61.8%

Solvents

methanol

Conditions

Workup

1. 1
   Otherthe solvent was evaporated in vacuo
2. 2
   Otherthe residue was triturated with ether
3. 3
   FiltrationThe white solid was filtered
4. 4
   Otherdried under vacuum overnight

Procedure

Chlorotrimethylsilane (3.96 mL, 31.2 mmol) was added dropwise to cis-2-aminocycloheptanecarboxylic acid (2.45 g, 15.6 mmol) in methanol (25 mL) at room temperature under nitrogen. After stirring for 2 h, the solvent was evaporated in vacuo and the residue was triturated with ether. The white solid was filtered and then dried under vacuum overnight to provide (1.65 g) cis-2-aminocycloheptanecarboxylic acid methyl ester: 1H NMR (CDCl3) δ 8.44 (s br, 2 H), 3.77 (s, 3 H), 3.62 (s br, 1 H), 3.27 (s br, 1 H), 2.20 (m, 2 H), 1.71 (m, 2 H), 1.66–1.47 (m, 6 H); MS m/e 172.26 (M+H)+.

Source