Ethyl Acetate → HCID 54472035, compound

HRID 1789847Notes

Reaction equation

HRID 1789847 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([CH3:22])[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O.[C:29]([OH:32])(=[S:31])[CH3:30]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([CH3:22])[CH:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][S:31][C:29](=[O:32])[CH3:30])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 53853843HCID 53853843, compoundHCID 178418634HCID 178418634, compound2×

Product 1

HCID 54472035HCID 54472035, compound

Conditions

Temperature
45 °C

Procedure

TEA (86 μL, 0.617 mmol) was added to a solution of 4-(2ethoxycarbonyl-1-methyl-allyl)-piperidine-1-carboxylic acid tert-butyl ester (0.18 g, 0.59 mmol) in thioacetic acid (2 mL) at 0° C. After stirring for 6 h more thioacetic acid (2 mL) was added and the mixture was stirred at 45° C. over night. EtOAc was added and the mixture was washed with water, saturated NaHCO3 and brine, dried and concentrated under reduced pressure. The crude was purified by flash chromatography (toluene/EtOAc, 5:1→1:1) to slightly unpure 4-(3-acetylsulfanyl-2-ethoxycarbonyl-1-methyl-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.17 g, 75%).

Workup

  1. additionwas added
  2. washthe mixture was washed with water, saturated NaHCO3 and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by flash chromatography (toluene/EtOAc, 5:1→1:1) to slightly unpure 4-(3-acetylsulfanyl-2-ethoxycarbonyl-1-methyl-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.17 g, 75%)

Sources & evidence

ORD record
ord-b53a6ec53d094e5881ace0eea6d99552
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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