Dimethylalumanylium chloride → 4-(Trifluoromethoxy)aniline

HRID 2381182Notes

Reaction equation

HRID 2381182 reaction equation
[C:1]1([CH3:33])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:15][CH2:14][C@H:13]([C:16](=[O:29])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[C:30]([OH:32])=[O:31])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:34][O:35][C:36]([C@H:38]1[CH2:43][CH2:42][N:41]([S:44]([C:47]2[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[C@H:40]([C:54]([OH:56])=[O:55])[CH2:39]1)=[O:37].[Cl-].C[Al+]C>CCCCCCC>[C:1]1([CH3:33])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:15][CH2:14][C@@H:13]([C:16](=[O:29])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[CH2:12][C@@H:11]2[C:30]([OH:32])=[O:31])(=[O:9])=[O:8])=[CH:5][CH:6]=1.[CH3:34][O:35][C:36]([C@@H:38]1[CH2:43][CH2:42][N:41]([S:44]([C:47]2[CH:48]=[CH:49][C:50]([CH3:53])=[CH:51][CH:52]=2)(=[O:45])=[O:46])[C@@H:40]([C:54]([OH:56])=[O:55])[CH2:39]1)=[O:37].[F:26][C:25]([F:27])([F:28])[O:24][C:21]1[CH:22]=[CH:23][C:18]([NH2:17])=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 16686359Dimethylalumanylium chlorideHCID 69811508HCID 69811508, compoundHCID 69812375HCID 69812375, compound

Product 3

HCID 6008484-(Trifluoromethoxy)anilineHCID 69811425HCID 69811425, compoundHCID 69813058HCID 69813058, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

In analogy to example 36 step B) the desired racemic mixture of (2S,4S)-1-(toluene-4-sulfonyl)-4-(4-trifluoromethoxy-phenylcarbamoyl)-piperidine-2-carboxylic acid and (2R,4R)-1-(toluene-4-sulfonyl)-4-(4-trifluoromethoxy-phenylcarbamoyl)-piperidine-2-carboxylic acid (0.22 g) was obtained from the reaction of a racemic mixture of (2S,4S)-1-(toluene-4-sulfonyl)-piperidine-2,4-dicarboxylic acid 4-methyl ester and (2R,4R)-1-(toluene-4-sulfonyl)-piperidine-2,4-dicarboxylic acid 4-methyl ester (0.392 g) with 4-trifluoromethoxy-aniline (0.264 g) and dimethylaluminium chloride in heptane (0.9 molar, 2.93 ml) as a brown solid. MS (ESI): 487.2 (MH+).

Sources & evidence

ORD record
ord-1feaf9a7f8784245b0ec1e1ab81632a4
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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