(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole → (S)-1-(2-chloro-4-nitroimidazol-1-yl)-3-{4-[2-(4-chlorophenyl)ethoxy]-piperidin-1-yl}-2-methyl-propan-2-ol

HRID 856259Notes

Reaction equation

HRID 856259 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][C@:11]2([CH3:14])[CH2:13][O:12]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][O:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:18][CH:17]=1>>[Cl:1][C:2]1[N:3]([CH2:10][C@@:11]([CH3:14])([OH:12])[CH2:13][N:28]2[CH2:27][CH2:26][CH:25]([O:24][CH2:23][CH2:22][C:19]3[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=3)[CH2:30][CH2:29]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

3

Reactant 2

HCID 10443353(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazoleHCID 694814924-[2-(4-Chlorophenyl)ethoxy]-piperidine

Product 1

HCID 69480555(S)-1-(2-chloro-4-nitroimidazol-1-yl)-3-{4-[2-(4-chlorophenyl)ethoxy]-piperidin-1-yl}-2-methyl-propan-2-olYield 71.4%

Procedure

Using (R)-2-chloro-1-(2-methyloxiran-2-yl-methyl)-4-nitroimidazole prepared in Example 12 (0.076 g, 0.350 mmol) and 4-[2-(4-chlorophenyl)ethoxy]-piperidine (0.080 g, 0.334 mmol) gave (S)-1-(2-chloro-4-nitroimidazol-1-yl)-3-{4-[2-(4-chlorophenyl)ethoxy]-piperidin-1-yl}-2-methyl-propan-2-ol (0.109 g, yield 71%) as a light yellow oil in the same manner as in Example 254.

Sources & evidence

ORD record
ord-15466493b04144c6a444d9deb66ea2e6
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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