Methanol → HCID 86639268, compound

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Reaction Steps

To a solution of (R)- or (S)-3-{4-[(E)-methoxyimino]-2,2-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl}-3H-imidazole-4-carboxylic acid methyl ester (ca. 100 mg, ca. 0.299 mmol), which can be prepared as described in Example 34, in dichloromethane (2 mL) at −78° C. is added DIBAL-H (1.0M in hexane, 0.91 mL, 0.91 mmol) portion wise over 45 minutes. Methanol (0.1 mL) is then added and the cooling bath is removed. The mixture is diluted with dichloromethane and an aqueous solution of Rochelle's salt is added. The mixture is vigorously stirred for 1 hour, further diluted with aqueous Rochelle's salt, then extracted with dichloromethane. The organic extract is dried over MgSO4, filtered, and concentrated to give a residue, which is purified by silica gel flash chromatography (dichloromethane-methanol, 97:3 to 19:1) to give (R)- or (S)-4-(5-hydroxymethyl-imidazol-1-yl)-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one O-methyl-oxime as a 19:1 mixture of geometric isomers; MS: (ESI) m/z 300.0 (M+H)+; 1H NMR (400 MHz, MeOD) of Major Isomer: δ ppm 0.96 (s, 3 H), 1.09 (s, 3 H), 2.71 (d, J=17.9 Hz, 1 H), 2.86 (d, J=17.9 Hz, 1 H), 4.06 (s, 3 H), 4.74 (d, J=13.9 Hz, 1 H), 4.78 (d, J=13.9 Hz, 1 H), 5.46 (s, 1 H), 6.99 (s, 1 H), 7.14-7.16 (m, 1 H), 7.22 (s, 1 H), 7.34-7.40 (m, 2 H), 8.11-8.15 (m, 1 H).

Provenance & Evidence