Water → HCID 54005589, compound

HRID 1682547Notes

Reaction equation

HRID 1682547 reaction equation
[H-].[Na+].[CH2:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br.[CH2:18]([O:20][C:21]([C@@H:23]1[CH2:28][CH2:27][CH2:26][N:25]([CH2:29][CH2:30]Br)[CH2:24]1)=[O:22])[CH3:19].O>C1(C)C=CC=CC=1>[CH2:18]([O:20][C:21]([C@@H:23]1[CH2:28][CH2:27][CH2:26][N:25]([CH2:29][CH2:30][O:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:24]1)=[O:22])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 242162-BenzylphenolHCID 24758Sodium hydrideHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

Product 1

HCID 54005589HCID 54005589, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (0.8 g, 20 mmol, 60% oil dispersion) was added portionwise to a stirred solution of 2-benzylphenol (1.8 g, 10 mmol) in toluene (30 ml) placed under an atmosphere of nitrogen. The mixture was stirred for 30 minutes and (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (3.5 g, 10 mmol, EP 374801) was added portionwise. The reaction mixture was stirred for 2 h at ambient temperature and water (50 ml) was added. The phases were separated and the organic phase was extracted with a 10% citric acid solution (200 ml). This acidic solution was extracted with a small portion of toluene and the organic extracts were discarded. To the acidic aqueous phase 4N sodium hydroxide was added until pH 7-8 and the mixture was extracted with ethyl acetate (150 ml). The organic extract was dried (Na2SO4) and the solvent was evaporated in vacuo to give 1.7 g of (R)-1-(2-(2-benzylphenoxy)ethyl)-3-piperidine-carboxylic acid ethyl ester as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 2 h at ambient temperature
  2. customThe phases were separated
  3. extractionthe organic phase was extracted with a 10% citric acid solution (200 ml)
  4. extractionThis acidic solution was extracted with a small portion of toluene
  5. additionTo the acidic aqueous phase 4N sodium hydroxide was added until pH 7-8
  6. extractionthe mixture was extracted with ethyl acetate (150 ml)
  7. extractionThe organic extract
  8. dry with materialwas dried (Na2SO4)
  9. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-854a50a40f0141fc8c183995e281634c
Source dataset
uspto-grants-1997_06
Patent number
US05635518

Reaction notes

Loading…