Sodium Hydroxide → [1-(4-Trifluoromethyl-phenyl)-piperidin-4-yloxy]-acetic acid tert-butyl ester

HRID 511072Notes

Reaction equation

HRID 511072 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:25]([O:24][C:22](=[O:23])[CH2:21][O:15][CH:12]1[CH2:13][CH2:14][N:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 220976741-[4-(Trifluoromethyl)phenyl]piperidin-4-ol

Product 1

HCID 58576326[1-(4-Trifluoromethyl-phenyl)-piperidin-4-yloxy]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Tetrabutylammonium bromide (275 mg; 0.85 mmol) is added to a solution of the crude 1-(4-trifluoromethyl-phenyl)-piperidin-4-ol (627 mg, prepared in accordance with Example 9) in toluene (8 mL). The reaction mixture is cooled to 0° C. and aq. 35% sodium hydroxide (8 mL) is added followed by a drop wise addition of tert-butyl bromoacetate (749 mg; 3.84 mmol).

Sources & evidence

ORD record
ord-7388af2873234ecb98ac2e46728b7e1d
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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