Pyrrolo[3,4-d]imidazole-5(1H)-carboxylic acid, 4,6-dihydro-2-methyl-, 1,1-dimethylethyl ester synthesis

8synthesis methods

Product Name:Pyrrolo[3,4-d]imidazole-5(1H)-carboxylic acid, 4,6-dihydro-2-methyl-, 1,1-dimethylethyl ester
CAS Number:1202067-73-9
Molecular formula:C11H17N3O2
Molecular Weight:223.27

Pyrrolo[3,4-d]imidazole-5(1H)-carboxylic acid, 3a,4,6,6a-tetrahydro-2-methyl-, 1,1-dimethylethyl ester, (3aR,6aS)-rel-

1202067-52-4
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Pyrrolo[3,4-d]imidazole-5(1H)-carboxylic acid, 4,6-dihydro-2-methyl-, 1,1-dimethylethyl ester

1202067-73-9
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Yield:1202067-73-9 62%

Reaction Conditions:

Stage #1: cis-(3,6)-2-methyl-3a,4,6,6a-tetrahydro-1H-pyrrolo[3.4-d]imidazole-5-carboxylic acid tert-butyl esterwith oxalyl dichloride;dimethyl sulfoxide in dichloromethane at -78; for 0.5 h;
Stage #2: with triethylamine in dichloromethane at -78 - 20;

Steps:

62

INTERMEDIATE 622-Methyl-4,6-dihydro-lH-pyrrolo[3,4-c/]imidazole-5-carboxylic acid tert-buty ester To a solution of oxalyl chloride (66.5 μL, 0.79 mmol) in DCM (7 mL), cooled to-78⁰C, was added dimethylsulfoxide (112 μL, 1.57 mmol) and the mixture was stirred for 10 minutes. After this time Intermediate 43 (177 mg, 0.79 mmol) in DCM (10 mL) was added and the mixture was stirred for a further 30 minutes. Triethylamine (50 mL) was then added and the mixture allowed to warm up to r.t. over 30 minutes. After this time the mixture was washed with saturated sodium bicarbonate solution (20 mL), the aqueous was extracted with DCM (3 x 50 mL), and the combined organics were dried (Na₂SO₄) and concentrated in vacuo. The crude product was purified by chromatography (SiO₂; 95:4.5:0.5 → 90:9:1 DCM/MeOH/28% aqueous NH₃) to obtain the title compound as a brown oil (109 mg, 62%). LCMS RT 1.46 minutes, (ES⁺) 224 (M+H)⁺.

References:

WO2009/153554,2009,A1 Location in patent:Page/Page column 58-59

73286-70-1 Synthesis

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114214-49-2
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rel-1,1-Dimethylethyl (3R,4S)-3,4-diazido-1-pyrrolidinecarboxylate

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1-Pyrrolidinecarboxylic acid, 3-azido-4-[(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester, (3S,4S)-

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References