4-[5-(1-Hydroxy-ethyl)-imidazol-1-yl]-3,3-dimethyl-isochroman-1-one → 4-(5-Acetyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

HRID 1690734Notes

Reaction equation

[OH:1][CH:2]([C:4]1[N:8]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[O:11][C:10]2([CH3:21])[CH3:20])[CH:7]=[N:6][CH:5]=1)[CH3:3]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[C:2]([C:4]1[N:8]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[O:11][C:10]2([CH3:21])[CH3:20])[CH:7]=[N:6][CH:5]=1)(=[O:1])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-[5-(1-hydroxy-ethyl)-imidazol-1-yl]-3,3-dimethyl-isochroman-1-one (0.100 g, 0.35 mmol) (Example 12) in dioxane (2 mL) is added manganese dioxide (0.46 g, 5.2 mmol) and the reaction mixture is heated to 60° C. overnight. Filtration through celite and concentration in vacuo gave a residue, which is purified by semi-preparative reverse phase HPLC to give 4-(5-acetyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; MS (ESI) m/z 285.0 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 1.22 (s, 3 H), 1.55 (s, 3 H), 2.61 (s, 3 H), 6.90 (s, 1 H), 7.38 (d, J=7.1 Hz, 1 H), 7.47 (s, 1 H), 7.57-7.62 (m, 1 H), 7.63-7.69 (m, 1 H), 7.93 (s, 1 H), 8.28 (dd, J=7.6, 1.5 Hz, 1 H).

Workup

filtrationFiltration
concentrationthrough celite and concentration in vacuo
customgave a residue, which
customis purified by semi-preparative reverse phase HPLC

Sources & evidence

ORD record: ord-d5869b4c95744cd881a52d7c292321ed
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153674B2

Reaction notes

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