Ethyl 3-hydroxybenzoate → 3-{2-[1-(3-Hydroxy-2,2-dimethyl-propionyl)-piperidin-4-yl]-ethoxy}-benzoic acid

HRID 2194637Notes

Reaction equation

HRID 2194637 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)([O:3]C(C)(C)C)=O.O[C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[C:21]([O:23]CC)=[O:22].N1CCC(CCOC2[CH:39]=[C:40]([CH:46]=CC=2)[C:41](OCC)=[O:42])CC1>>[OH:42][CH2:41][C:40]([CH3:46])([CH3:39])[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][O:16][C:27]2[CH:26]=[C:20]([CH:19]=[CH:18][CH:28]=2)[C:21]([OH:23])=[O:22])[CH2:12][CH2:13]1)=[O:3]

Participants

4

Reactant 3

HCID 24522Ethyl 3-hydroxybenzoateHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 56830235Ethyl 3-(2-piperidin-4-yl-ethoxy)-benzoate

Product 1

HCID 687820493-{2-[1-(3-Hydroxy-2,2-dimethyl-propionyl)-piperidin-4-yl]-ethoxy}-benzoic acid

Procedure

Prepared from N-Boc-4-piperidine ethanol and ethyl 3-hydroxybenzoate, with the exception that ethyl 3-(2-piperidin-4-yl-ethoxy)-benzoate was converted to its corresponding carboxamide as described below before the final alkaline hydrolysis to give the title compound. LC-MS (m/z): 351 (M+2).

Workup

  1. customalkaline hydrolysis

Sources & evidence

ORD record
ord-68c66e7ccc4e485a9c38145e34e61507
Source dataset
uspto-grants-2012_12
Patent number
US08334305B2

Reaction notes

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