| Identification | Back Directory | [Name]
tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate | [CAS]
1226781-82-3 | [Synonyms]
CPD0232
MK-3103 Intermediate IV
Omarigliptin Impurity 10
Omarigliptin Intermediate 3
5-Boc-2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole
tert-butyl 2-methanesulfonyl-2H,4H,5H,6H-pyrrolo[3,4-c]pyrazole-5-carboxylate
Pyrrolo[3,4-c]pyrazole, 2,4,5,6-tetrahydro-2-(methylsulfonyl)-, benzenesulfonate
tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate
tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate
2-(Methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylic acid tert-butyl ester
Pyrrolo[3,4-c]pyrazole-5(4H)-carboxylic acid, 2,6-dihydro-2-(methylsulfonyl)-, 1,1-dimethylethyl ester | [Molecular Formula]
C11H17N3O4S | [MDL Number]
MFCD24467621 | [MOL File]
1226781-82-3.mol | [Molecular Weight]
287.34 |
| Chemical Properties | Back Directory | [Boiling point ]
441.1±55.0 °C(Predicted) | [density ]
1.40±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [pka]
-1.95±0.20(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C11H17N3O4S/c1-11(2,3)18-10(15)13-5-8-6-14(19(4,16)17)12-9(8)7-13/h6H,5,7H2,1-4H3 | [InChIKey]
SNEHALFDVXIDSZ-UHFFFAOYSA-N | [SMILES]
N1(S(C)(=O)=O)C=C2CN(C(OC(C)(C)C)=O)CC2=N1 |
| Hazard Information | Back Directory | [Chemical Properties]
white solid | [Uses]
Tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate is an important organic reagent that can be used as a building block for the synthesis of many organic compounds, such as 2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole. It is an important intermediate of Omarigliptin.
![tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate](/NewsImg/2023-10-17/6383313930512510309750544.jpg "tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate") | [Synthesis]
Tert-butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate (3.5 g, 16.7 mmol) was dissolved in tetrahydrofuran (35 ml), and sodium hydride (1.0 g, 60%, 25.4 mmol) was added at 0°C, followed by reaction for 30 min. Methylsulfonyl chloride (2.9 g, 25.4 mmol) was added, followed by a reaction for 1 hour. The reaction was quenched by the addition of water (10 ml) to the reaction solution, which was extracted with ethyl acetate (50 ml*2). The organic layers were combined, dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column chromatography (petroleum ether/ethyl acetate (v/v) = 1:1), to obtain tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate (2.1 g, yield 44%).![tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate](/NewsImg/2023-10-17/6383313814796791749926853.jpg "tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate") | [References]
[1] Patent: EP3159344, 2017, A1. Location in patent: Paragraph 0096; 0132; 0133
[2] Patent: TW2017/8222, 2017, A. Location in patent: Page/Page column 54; 55
[3] Patent: TW2017/8223, 2017, A. Location in patent: Page/Page column 43
[4] Patent: WO2011/103256, 2011, A1. Location in patent: Page/Page column 55
[5] Patent: WO2011/146358, 2011, A1. Location in patent: Page/Page column 61 |
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