Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-7-hydroxy-, (7R-cis)- (9CI) synthesis

2synthesis methods

Product Name:Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-7-hydroxy-, (7R-cis)- (9CI)
CAS Number:107676-54-0
Molecular formula:C7H10N2O3
Molecular Weight:170.17

(2S,4R)-N-tert-butoxycarbonylaminoacetyl-4-hydroxyproline methyl ester

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Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-7-hydroxy-, (7R-cis)- (9CI)

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Yield:107676-54-0 100%

Reaction Conditions:

Stage #1: (2S,4R)-N-tert-butoxycarbonylaminoacetyl-4-hydroxyproline methyl esterwith trifluoroacetic acid in dichloromethane at 20; for 2 h;
Stage #2: with sodium hydrogencarbonate in dichloromethane;water;

Steps:

7.b

To a solution of the compound obtained in the previous section (1.3 g, 4.30 mmol) in CH₂CI₂ (2 mL), thfluoroacetic acid (1 mL) was added. The solution was stirred at room temperature for 2 h. A 2N aqueous NaHCO3 solution (2 ml_) was added and the mixture evaporated to dryness. The crude product was diluted with a mixture of CHCI₃/MeOH/NH₃ (10:5:1 , 10 ml_) and the solution thus obtained was filtered over silica gel. The filtrate was concentrated to dryness to afford the desired compound in quantitative yield.LC-MS (method 2): t_R = 0.28 min; m/z = 171.2 (MH⁺).

References:

WO2008/119792,2008,A1 Location in patent:Page/Page column 71-72

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References