Methanol → Ethyl 2-aminocyclopent-1-ene-1-carboxylate

HRID 1757090Notes

Reaction equation

HRID 1757090 reaction equation
C(OC([NH:6][C:7]1[CH2:11][CH2:10][CH2:9][C:8]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=O)C.C[O-].[Na+].CO>O>[NH2:6][C:7]1[CH2:11][CH2:10][CH2:9][C:8]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 53935635HCID 53935635, compound

Product 1

HCID 243333Ethyl 2-aminocyclopent-1-ene-1-carboxylateYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution containing ethyl 2-[(ethoxycarbonyl)amino]-1-cyclopentene-1-carboxylate (72 g, 0.32 moles) and 25 wt % sodium methoxide in methanol (91.5 mL, 0.40 moles) was refluxed for about 18 hours. Methanol (200 mL) was added during the course of the reaction. The reaction mixture was allowed to cool to ambient temperature then diluted with water and extracted with diethyl ether (5×100 mL). The ether extracts were combined, treated with activated charcoal, dried over sodium sulfate then evaporated to provide 43.8 g of ethyl 2-amino-1-cyclopentene-1-carboxylate as an ivory solid, m.p. 90°-92° C.

Workup

  1. temperaturewas refluxed for about 18 hours
  2. extractionextracted with diethyl ether (5×100 mL)
  3. additiontreated with activated charcoal
  4. dry with materialdried over sodium sulfate
  5. customthen evaporated

Sources & evidence

ORD record
ord-7afe1690a7f34d4fbaefe97eaa099e93
Source dataset
uspto-grants-1995_08
Patent number
US05444065

Reaction notes

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