Acetic Acid → Piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3-benzyl 3-(3,3-dimethyl-2-oxobutyl)ester

HRID 2407497Notes

Reaction equation

[CH2:1]([O:8][C:9]([C:11]1([C:25]([OH:27])=[O:26])[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38].C(O)(=O)C>CN(C)C=O>[CH3:38][C:37]([CH3:40])([CH3:39])[C:36](=[O:41])[CH2:35][O:26][C:25]([C:11]1([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:22])[Cl:23])=[O:18])[CH2:12]1)=[O:27]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3-benzyl ester (3.9 g 8.8 mmol), potassium carbonate (1.83 g 13 mmol) and bromopinacolone (2.31 g 13 mmol) in N,N-dimethylformamide (55 mL) is heated at 60° C. for 2 h. The mixture is cooled back to room temperature, neutralized with acetic acid (13 mmol) and concentrated under reduced pressure. the residue is dissolved in ethyl acetate, washed with water and concentrated. Cristallization in diethyl oxide gives piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3-benzyl 3-(3,3-dimethyl-2-oxobutyl)ester melting at 114° C.

Workup

temperatureThe mixture is cooled back to room temperature
concentrationconcentrated under reduced pressure
dissolutionthe residue is dissolved in ethyl acetate
washwashed with water
concentrationconcentrated

Sources & evidence

ORD record: ord-f4e866575fe042558d2586bb75feea1b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809539B2

Reaction notes

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