(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole → (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(3-phenyl-2-propenyloxy)piperidin-1-yl]propan-2-ol

HRID 856256Notes

Reaction equation

HRID 856256 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.[C:15]1([CH:21]=[CH:22][CH2:23][O:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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][CH:22]=[CH:21][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][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 537562574-[(3-Phenylprop-2-en-1-yl)oxy]piperidine

Product 1

HCID 69479626(S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(3-phenyl-2-propenyloxy)piperidin-1-yl]propan-2-olYield 49%

Procedure

Using (R)-2-chloro-1-(2-methyloxiran-2-yl-methyl)-4-nitroimidazole prepared in Example 12 (0.198 g, 0.910 mmol) and 4-(3-phenyl-2-propenyloxy)piperidine (0.198 g, 0.910 mmol) gave (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(3-phenyl-2-propenyloxy)piperidin-1-yl]propan-2-ol (0.192 g, yield 49%) as a brown oil in the same manner as in Example 254.

Sources & evidence

ORD record
ord-aa86f832d20d48c4a4c727de7fe09491
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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