Triethylamine → tert-butyl 7-(1-phenyl-1H-tetrazol-5-yl)-2,7-diazaspiro[4.4]nonane-2-carboxylate

HRID 1182685Notes

Reaction equation

CCN(CC)CC.[CH2:8]1[C:12]2([CH2:16][CH2:15][NH:14][CH2:13]2)[CH2:11][CH2:10][N:9]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].Cl[C:25]1[N:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:28]=[N:27][N:26]=1>O1CCOCC1>[C:30]1([N:29]2[C:25]([N:14]3[CH2:15][CH2:16][C:12]4([CH2:8][N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:10][CH2:11]4)[CH2:13]3)=[N:26][N:27]=[N:28]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 115 °C

Procedure

Et3N (5 mL) was added into a solution of tert-butyl 2,7-diazaspiro[4.4]nonane-2-carboxylate (1 g) and 5-chloro-1-phenyl-1H-tetrazole (1 g) in dioxane (50 mL). The mixture was heated to 115° C. for 24 hours. The reaction was quenched with water (50 mL). The aqueous layer was extracted with EtOAc (3×50 mL). The combined organic phase was dried over MgSO4 and concentrated to give a residue which was purified by silica gel chromatography to give tert-butyl 7-(1-phenyl-1H-tetrazol-5-yl)-2,7-diazaspiro[4.4]nonane-2-carboxylate.

Workup

customThe reaction was quenched with water (50 mL)
extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
dry with materialThe combined organic phase was dried over MgSO4
concentrationconcentrated
customto give a residue which
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-9c9ca475cc9849118ddac77e2d61125e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664213B2

Reaction notes

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