Sodium hydride → 4-[4-(4-Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 2100676Notes

Reaction equation

HRID 2100676 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][C:25]=1[C:32]([F:35])([F:34])[F:33].CCOC(C)=O.CCCCCC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:30][C:27]3[CH:28]=[CH:29][C:24]([Cl:23])=[C:25]([C:32]([F:35])([F:33])[F:34])[CH:26]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 130942621-Chloro-4-(chloromethyl)-2-(trifluoromethyl)benzeneHCID 19381871tert-Butyl 4-(4-hydroxyphenyl)piperidine-1-carboxylateHCID 21226206Ethyl acetate hexane

Product 1

HCID 688130084-[4-(4-Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (1 eq) in anhydrous DMF is added NaH (1.1 eq) at room temperature. After 5 minutes, 1-chloro-4-chloromethyl-2-trifluoromethyl-benzene (1.1 eq) in DMF is added. The resulting mixture is stirred for 30 minutes. After aqueous work up, flash column chromatography (10% EtOAc/hexane) gave 4-[4-(4-Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester. [MS: (ES+) 490.3 (M+1)+].

Sources & evidence

ORD record
ord-bf04a82c275c4d249655d7ad175aa930
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

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