Methyl 3-oxo-4-{4-[(trityloxy)methyl]-2-cyclopenten-1-yl}-3,4-dihydro-2-pyrazinecarboxylate → Methyl 4-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate
Reaction equation
[O:1]=[C:2]1[N:7]([CH:8]2[CH2:12][CH:11]([CH2:13][O:14]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:10]=[CH:9]2)[CH:6]=[CH:5][N:4]=[C:3]1[C:34]([O:36][CH3:37])=[O:35]>C(O)(=O)C.O>[OH:14][CH2:13][CH:11]1[CH2:12][CH:8]([N:7]2[CH:6]=[CH:5][N:4]=[C:3]([C:34]([O:36][CH3:37])=[O:35])[C:2]2=[O:1])[CH:9]=[CH:10]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
In 2.0 mL of 80% aqueous solution of acetic acid was dissolved 0.20 g of methyl 3-oxo-4-{4-[(trityloxy)methyl]-2-cyclopenten-1-yl}-3,4-dihydro-2-pyrazinecarboxylate, and the solution thus obtained was heated at 80° C. for one hour. The reaction mixture was allowed to cool and diluted with 10 mL of water, the deposited precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography [eluent: ethyl acetate] to obtain 77 mg of methyl 4-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate as a light yellow oily product.
Workup
- customthe solution thus obtained
- temperatureto cool
- filtrationthe deposited precipitate was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by column chromatography [eluent: ethyl acetate]
Sources & evidence
- ORD record
- ord-cd92d3cdb6924eaebcba76302106ce18
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06800629B2
Reaction notes
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