Chlorotrimethylsilane → cis-2-Aminocycloheptanecarboxylic acid methyl ester

HRID 7022Notes

Reaction equation

HRID 7022 reaction equation
Cl[Si](C)(C)[CH3:3].[NH2:6][C@H:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[C:14]([OH:16])=[O:15]>CO>[CH3:3][O:15][C:14]([C@@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:7]1[NH2:6])=[O:16]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 2734693(1R,2S)-2-aminocycloheptane-1-carboxylic acid

Product 1

HCID 1512672cis-2-Aminocycloheptanecarboxylic acid methyl esterYield 61.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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)+.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customthe residue was triturated with ether
  3. filtrationThe white solid was filtered
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-e56c1f2df7514a04a72d834c171ea357
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Reaction notes

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