Toluene → 2-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid

HRID 227597Notes

Reaction equation

HRID 227597 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=[O:6].[N:19]1(CO)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[C:27]([O-:30])([O-])=O.[K+].[K+].[C:33]1(C)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[OH:30][C:27]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:22]1[CH2:21][CH2:20][N:19]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=2)=[O:6])[CH2:24][CH2:23]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 446909Piperidin-1-ylmethanolHCID 109235672-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid

Product 1

HCID 99356992-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid

Procedure

A mixture of 800 mg of 4-(4-chloro-1-oxobutyl)-α,α-dimethylphenylacetic acid, prepared in accordance with Example 4, 800 mg of 4-α,α-diphenyl)piperidinemethanol, and 2.4 g of K2CO3 in 25 mL of toluene is stirred for 48 hours at room temperature. The mixture is concentrated in vacuo. The residue is treated with EtOAc, filtered, and concentrated to afford 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylphenylacetic acid.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additionThe residue is treated with EtOAc
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4b1c7d2bdf53448db2d485e81f802f5e
Source dataset
uspto-grants-2009_07
Patent number
US07560561B2

Reaction notes

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