Tributylvinyltin → 1-[1-(Tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(5-vinyl-2-thiophenesulfonyl)-2-piperazinone

HRID 1840577Notes

Reaction equation

HRID 1840577 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:12](=[O:30])[CH2:11]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[CH:31]([Sn](CCCC)(CCCC)CCCC)=[CH2:32].[Cl-].[Li+]>O1CCOCC1>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([CH2:16][N:13]2[CH2:14][CH2:15][N:10]([S:7]([C:5]3[S:6][C:2]([CH:31]=[CH2:32])=[CH:3][CH:4]=3)(=[O:9])=[O:8])[CH2:11][C:12]2=[O:30])[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 234475704-(5-Bromo-2-thiophenesulfonyl)-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone

Product 1

HCID 234473631-[1-(Tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(5-vinyl-2-thiophenesulfonyl)-2-piperazinoneYield 116.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(5-bromo-2-thiophenesulfonyl)-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (200 mg), vinyltributyltin (365 mg), lithium chloride (50 mg), tetrakistriphenylphosphine palladium (50 mg) and dioxane (15 ml) was refluxed for 2 hours. The reaction solution was concentrated, and the residue was purified with silica gel column chromatography (hexane: ethyl acetate=1:2) to give colorless solid of 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(5-vinyl-2-thiophenesulfonyl)-2-piperazinone (209 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was purified with silica gel column chromatography (hexane: ethyl acetate=1:2)

Sources & evidence

ORD record
ord-5a4873734c9f4d299705c1c8a75b5679
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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