Toluene → 2-Oxo-3-(4-phenyl-butyl)-3,10-diaza-bicyclo[4.3.1]dec-4-ene-10-carboxylic Acid 9H-Fluoren-9-ylmethyl Ester

HRID 987098Notes

Reaction equation

HRID 987098 reaction equation
C1C2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH:23]([C:24](=[O:36])[NH:25][CH2:26][CH2:27][CH2:28]CC4C=CC=CC=4)[CH2:22][CH2:21][CH2:20][CH:19]3[CH2:37][CH:38](OC)OC)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9]C=3)C=2C=CC=1.[C:43]1([CH3:53])[CH:48]=[CH:47][C:46](S([O-])(=O)=O)=[CH:45][CH:44]=1.[NH+]1C=CC=CC=1.[C:60]1([CH3:66])[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>>[CH:47]1[C:48]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH:19]4[CH2:20][CH2:21][CH2:22][CH:23]3[C:24](=[O:36])[N:25]([CH2:26][CH2:27][CH2:28][CH2:66][C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[CH:38]=[CH:37]4)=[O:17])[C:11]3[C:53](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:43]=2[CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 213636312-(2,2-Dimethoxy-ethyl)-6-(4-phenyl-butylcarbamoyl)-piperidine-1-carboxylic Acid 9H-fluoren-9-ylmethyl Ester2×

Product 1

HCID 545179472-Oxo-3-(4-phenyl-butyl)-3,10-diaza-bicyclo[4.3.1]dec-4-ene-10-carboxylic Acid 9H-Fluoren-9-ylmethyl EsterYield 87%

Conditions

Temperature
100 °C

Procedure

2-(2,2-Dimethoxy-ethyl)-6-(4-phenyl-butylcarbamoyl)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (Compound 243, 1 g, 1.75 mmol) was dissolved in toluene (25 ml). Pyridinium p-toluene sulfonate (0.02 g, 0.08 mmol) was added and the reaction was stirred at 100° C. for 2 hours. After this time the reaction was cooled down, the toluene was evaporated and the residue was dissolved in EtOAc (75 mL), washed with saturated NaHCO3 solution (25 mL) and dried over Na2SO4. Flash chromatographic purification of the residue (1:2 EtOAc/hexanes) gave Compound 244 (0.770 g, 87%). Rf=0.5 (1:2 EtOAc/hexanes).

Workup

  1. temperatureAfter this time the reaction was cooled down
  2. customthe toluene was evaporated
  3. dissolutionthe residue was dissolved in EtOAc (75 mL)
  4. washwashed with saturated NaHCO3 solution (25 mL)
  5. dry with materialdried over Na2SO4
  6. customFlash chromatographic purification of the residue (1:2 EtOAc/hexanes)

Sources & evidence

ORD record
ord-908ee5a4d4284ae19ced5e57f1347dee
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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