Water → HCID 53697013, compound

HRID 1789791Notes

Reaction equation

HRID 1789791 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][SH:46])=[CH:41][CH:40]=1.O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:16]([S:46][CH2:45][C:42]2[CH:43]=[CH:44][C:39]([O:38][CH3:37])=[CH:40][CH:41]=2)[CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 804074-Methoxy-alpha-toluenethiolHCID 54364525HCID 54364525, compound

Product 1

HCID 53697013HCID 53697013, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
75 °C

Procedure

4-(2-tert-Butoxycarbonyl4-phenyl-but-2-enyl)-piperidine-1-carboxylic acid tert-butyl ester (0.8 g, 1.93 mmol) in DMF (10 mL) was added to a suspension of potassium carbonate (0.20 g, 1.44 mmol) ) and 4-methoxy-α-toluenethiol (0.54 mL, 3.85 mmol) in DMF (10 mL) under nitrogen. The mixture was heated to 75° C. for 24 h and allowed to cool to room temperature. The reaction mixture was then poured into H2O and extracted with ethyl acetate. The organic layers were combined and washed with water. The organic layer was dried, filtered, and concentrated under reduced pressure to give 1.8 g crude material. The crude product was purified by column chromatography (ethyl acetate/hexane, 1:10) to give 4-[2-tert-butoxycarbonyl-3-(4-methoxy-benzylsulfanyl)4-phenyl-butyl]-piperidine-1-carboxylic acid tert-butyl ester (0.55 g, 50%).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give 1.8 g crude material
  8. customThe crude product was purified by column chromatography (ethyl acetate/hexane, 1:10)

Sources & evidence

ORD record
ord-6952928057324816a1938954f85bcf59
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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