1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Azidomethyl-4-methyl-1-tritylimidazole

HRID 1584255Notes

Reaction equation

[C:1]([N:20]1[C:24]([CH2:25]O)=[C:23]([CH3:27])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P([N:42]=[N+:43]=[N-:44])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:42]([CH2:25][C:24]1[N:20]([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:21]=[N:22][C:23]=1[CH3:27])=[N+:43]=[N-:44]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-trityl-4-methyl-5-imidazolemethanol (3.7 g, 10 mmol) and DPPA (3.0 ml, 13 mmol) in THF (100 ml) was added DBU (2.0 ml, 13 mmol). The resulting solution was heated to 60° C. for 2 h. The solvents were removed in vacuo and the residue purified by flash chromatography (2:1 hexane/ethyl acetate) to give of the title compound. 1H NMR (CDCl3) d 1.42 (s, 3 H), 4.22 (s, 2 H), 7.10-7.35 (m, 16 H).

Workup

customThe solvents were removed in vacuo
customthe residue purified by flash chromatography (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-07c82abb677c45e7bfcab23c1c4499b5
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932606

Reaction notes

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