Hydrochloric Acid → (1S,4R)-Methyl 4-aminocyclopent-2-enecarboxylate hydrochloride

HRID 1823341Notes

Reaction equation

HRID 1823341 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:8])[NH:2]2.[CH3:9][OH:10].[ClH:11]>C1(C)C=CC=CC=1>[ClH:11].[CH3:9][O:10][C:3]([C@H:4]1[CH2:7][C@@H:1]([NH2:2])[CH:6]=[CH:5]1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-one

Product 1

HCID 60152708(1S,4R)-Methyl 4-aminocyclopent-2-enecarboxylate hydrochlorideYield 94.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.0 g (183.3 mmol) of 2-azabicyclo[2.2.1]hept-5-en-3-one, 8.8 g (274.7 mmol) of methanol, and 150 mL of toluene were put into a four-necked flask (300 mL volume) equipped with a hydrogen chloride introducing tube, a thermometer, and an exhaust tube. 6.7 g (183.8 mmol) of hydrogen chloride was introduced into the obtained mixture over a period of 2 hours through the hydrogen chloride introducing tube at room temperature. Following 1 hour of stirring, the precipitated crystals were filtered off with a glass filter. The obtained crystals were dried under reduced pressure to give 30.8 g (173.2 mmol) of cis-4-amino-2-cyclopentene-1-carboxylic acid methyl ester hydrochloride (that is, (1S*, 4R*)-4-amino-1-methoxycarbonyl-2-cyclopentene hydrochloride). The yield was 94.4%.

Workup

  1. custom(300 mL volume) equipped with a hydrogen chloride introducing tube
  2. filtrationthe precipitated crystals were filtered off with a glass
  3. filtrationfilter
  4. customThe obtained crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-1fd5e2f254834344aa4798c885212082
Source dataset
uspto-grants-2006_05
Patent number
US07038059B2

Reaction notes

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