Hydrochloric Acid → 4-[1-Hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-alpha-(hydroxymethyl)-alpha-methyl-benzeneacetic Acid

HRID 48025Notes

Reaction equation

HRID 48025 reaction equation
[OH:1][CH:2]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH2:39][OH:40])([CH3:38])[C:33]([O:35]CC)=[O:34])=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.[OH-].[Na+].Cl>CO.O1CCCC1>[OH:1][CH:2]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH2:39][OH:40])([CH3:38])[C:33]([OH:35])=[O:34])=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:25])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 98936614-[1-Hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-alpha-(hydroxymethyl)-alpha-methyl-benzeneacetic acid, ethyl ester

Product 1

HCID 102795274-[1-Hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-alpha-(hydroxymethyl)-alpha-methyl-benzeneacetic AcidYield 66.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-α-(hydroxymethyl)-α-methyl-benzeneacetic acid, ethyl ester (200 mg, 0.37 mmol) in methanol (8 mL) and tetrahydrofuran (12 mL). Add 1.6 mL (1.6 mmol) of a 1 molar solution of aqueous sodium hydroxide. After 4 hours, cool the solution to room temperature and add 10% hydrochloric acid (ca. 1 mL) dropwise until pH is 5-6. Concentrate the solution and purify by flash chromatography (50 g of silica gel, methanol/chloroform gradient elution) to give the title compound (127 mg, 66%). Additionally, the following compounds can be prepared by the synthetic procedure depicted in Step J:

Workup

  1. concentrationConcentrate the solution
  2. custompurify by flash chromatography (50 g of silica gel, methanol/chloroform gradient elution)

Sources & evidence

ORD record
ord-7dfe722baa7e4e68bb8c5a038291cdfd
Source dataset
uspto-grants-2004_03
Patent number
US06700012B2

Reaction notes

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