Ethyl orthoformate → methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate

HRID 2173367Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:5]2=[CH:4][CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+].[CH:19](OCC)(OCC)OCC>CC(O)=O>[N:1]1([C:2]2[N:7]=[C:6]3[CH2:8][CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:5]3=[CH:4][CH:3]=2)[CH:19]=[N:17][N:16]=[N:15]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a flask charged with methyl 2-amino-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate (500 mg, 2.6 mmol) and a stir bar was added sodium azide (340 mg, 5.2 mmol), triethyl orthoformate (2.2 mL, 13 mmol), and HOAc (10 mL). The mixture was heated to 100° C. for 2 hours. The solvent was removed on a rotavapor, and the residue was taken into aq. Sodium carbonate, extracted with EtOAc (50 Mk×3), dried over sodium sulfate, and purified by MPLC (DCM-MeOH). After removal of solvent, an off-white solid was collected as the desired methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate. LC-MS (IE, m/z): 248 [M+1]+;

Workup

customThe solvent was removed on a rotavapor
extractionextracted with EtOAc (50 Mk×3),
dry with materialdried over sodium sulfate
custompurified by MPLC (DCM-MeOH)
customAfter removal of solvent
customan off-white solid was collected as the desired methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate

Sources & evidence

ORD record: ord-195fe87543f349ae98e05f4c6dbcb2d7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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