1,8-Diazabicyclo(5.4.0)undec-7-ene → 1,4-Bis(tert-butoxycarbonyl)-2-[3-(thien-2-yl)-2-propenyl]piperazine

HRID 352832Notes

Reaction equation

HRID 352832 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[CH2:21][CH:22]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][PH3+].C1CCN2C(=NCCC2)CC1>O1CCCC1.C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[CH2:21][CH:22]=[CH:29][C:25]1[S:24][CH:28]=[CH:27][CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22709630[(Thien-2-yl)methyl]phosphoniumHCID 227100181,4-Bis(tert-butoxycarbonyl)-2-formylmethylpiperazine

Product 1

HCID 698800971,4-Bis(tert-butoxycarbonyl)-2-[3-(thien-2-yl)-2-propenyl]piperazine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (50 ml) was dissolved 1,4-bis(tert-butoxycarbonyl)-2-formylmethylpiperazine (1.01 g). Under ice cooling, a solution of [(thien-2-yl)methyl]phosphonium (1.62 g) in chloroform (100 ml) was added to the resulting solution, followed by the dropwise addition of 1,8-diazabicyclo[5.4.0]-7-undecene (620 μl). The resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was distilled under reduced pressure. The residue was subjected to chromatography on a silica gel column (hexane:ethyl acetate=9:1 to 2:1), whereby the title compound (1.13 g) was obtained as a pale yellow oil.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customwas obtained as a pale yellow oil

Sources & evidence

ORD record
ord-f3d437efcc9c4175a3c88a395be7e8fa
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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