Stannane, tributyl(1-ethoxyethenyl)- → HCID 125496709, compound

HRID 1010877Notes

Reaction equation

HRID 1010877 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:23]([O:25]CC)=[CH2:24])CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([C:23](=[O:25])[CH3:24])=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate

Product 1

HCID 125496709HCID 125496709, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 600 mg of the compound [1-1], 75 mg of dichlorobis(triphenylphosphine)palladium (II), 743 μL of tributyl (1-ethoxyvinyl)tin, and 3 mL of 1,4-dioxane, was stirred overnight at 100° C. After standing to cool, the insolubles were filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=8/2) to obtain 367 mg of tert-butyl[(1S)-1-(4-acetylphenyl)ethyl]carbamate [1-2] (hereinafter, referred to as the compound [1-2]) as a colorless solid.

Workup

  1. temperatureto cool
  2. filtrationthe insolubles were filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=8/2)

Sources & evidence

ORD record
ord-397c69447bc64d76ad78dbeb45786b65
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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