Imidazole-1-carboxylic acid 4-trifluoromethylbenzyl ester → 3-[3-(Ethoxycarbonylmethyl-amino)-4-methyl-phenyl]-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester

HRID 1269550Notes

Reaction equation

HRID 1269550 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)[CH:10]=[CH:9][C:8]=1[CH3:19])[CH3:2].[F:21][C:22]([F:39])([F:38])[C:23]1[CH:37]=[CH:36][C:26]([CH2:27][O:28][C:29](N2C=CN=C2)=[O:30])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[F:21][C:22]([F:38])([F:39])[C:23]1[CH:37]=[CH:36][C:26]([CH2:27][O:28][C:29]([N:15]2[CH2:16][CH2:17][CH2:18][CH:13]([C:11]3[CH:10]=[CH:9][C:8]([CH3:19])=[C:7]([NH:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:20])[CH:12]=3)[CH2:14]2)=[O:30])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 68882567Imidazole-1-carboxylic acid 4-trifluoromethylbenzyl esterHCID 68883656(2-Methyl-5-piperidin-3-ylphenylamino)acetic acid ethyl ester

Product 1

HCID 688837423-[3-(Ethoxycarbonylmethyl-amino)-4-methyl-phenyl]-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl esterYield 37%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2-Methyl-5-piperidin-3-yl-phenylamino)-acetic acid ethyl ester (63 mg, 0.23 mmol) was dissolved in 3 mL toluene and imidazole-1-carboxylic acid 4-trifluoromethyl-benzyl ester (93 mg, 0.34 mmol) was added. The reaction was stirred for 18 h at room temperature under nitrogen. The reaction was flash chromatographed with 15% ethyl acetate/hexanes to yield 40 mg (37%) of the desired 3-[3-(ethoxycarbonylmethyl-amino)-4-methyl-phenyl]-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester as a clear oil.

Workup

  1. customchromatographed with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ebe148277ff24b71b33dba4d43f67b6d
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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