1,5-Diazabicyclo(4.3.0)non-5-ene → N-{[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1258583Notes

Reaction equation

[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1CN2C(=NCCC2)C1.Br.[Br-].[O:27]1[CH2:31][CH2:30][O:29][CH:28]1[C:32]1[N:37]=[C:36]([CH2:38][N+]2C=CC=CC=2)[CH:35]=[CH:34][CH:33]=1>CC#N>[O:27]1[CH2:31][CH2:30][O:29][CH:28]1[C:32]1[N:37]=[C:36]([CH2:38][O:1][N:2]=[C:3]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (12.2 g, 60.03 mmol, 1.0 eq.) in 250 ml of MeCN, was added dropwise DBN (12.30 g, 99.06 mmol, 1.65 eq.). The reaction was stirred for 5 mins before addition of 1-{[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromide (15.7 g, 39.02 mmol, 0.65 eq.) portionwise. The mixture was stirred for further 5 mins before removal of the cooling bath and continued at ambient temperature. MeCN was evaporated and the residue dissolved in 500 ml of DCM, washed with water (×2), dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to yield N-{[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (5 g, 22% yield) as a pale yellow oil.

Workup

customcontinued at ambient temperature
customMeCN was evaporated
dissolutionthe residue dissolved in 500 ml of DCM
washwashed with water (×2)
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-f4a633d89ae54882a212a45eabedec58
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466176B2

Reaction notes

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