Water → HCID 54149643, compound

HRID 1789790Notes

Reaction equation

HRID 1789790 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][SH:43])=[CH:38][CH:37]=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:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH:16]([S:43][CH2:42][C:39]2[CH:40]=[CH:41][C:36]([O:35][CH3:34])=[CH:37][CH:38]=2)[CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 804074-Methoxy-alpha-toluenethiolHCID 54243196HCID 54243196, compound

Product 1

HCID 54149643HCID 54149643, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-(2-tert-butoxycarbonyl-5-methyl-hex-2-enyl)-piperidine-1-carboxylic acid tert-butyl ester (2.0 g, 5.24 mmol) in DMF (5 mL) was added to a mixture of potassium carbonate (0.54 g, 3.93 mmol) and 4-methoxy-α-toluenethiol (1.17 g, 10.48 mmol) in DMF (50 mL) under nitrogen. The mixture was refluxed for 5 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 3.76 g of 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)-5-methyl-hexyl]-piperidine-1-carboxylic acid tert-butyl ester (1.77 g, 63%).

Workup

  1. temperatureThe mixture was refluxed for 5 h
  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 3.76 g of crude material
  8. customThe crude product was purified by column chromatography (ethyl acetate/hexane, 1:10)

Sources & evidence

ORD record
ord-c358a21ea0d542caa5807df5d9aaba60
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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