1,4-Bis(tert-butoxycarbonyl)-2-[3-(thien-2-yl)-2-propenyl]piperazine → 1,4-Bis(tert-butoxycarbonyl)-2-[3-(thien-2-yl)propyl]piperazine

HRID 352833Notes

Reaction equation

HRID 352833 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]=[CH:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][CH:9]1[CH2:21][CH2:22][CH2:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

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

Product 1

HCID 227104421,4-Bis(tert-butoxycarbonyl)-2-[3-(thien-2-yl)propyl]piperazine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In methanol (70 ml) was dissolved 1,4-bis(tert-butoxycarbonyl)-2-[3-(thien-2-yl)-2-propenyl]piperazine (1.01 g). In the resulting solution was suspended 10% palladium-carbon (50% wet, 431 mg), followed by vigorous shaking at room temperature for 6 hours under a hydrogen gas atmosphere of 1 atmospheric pressure. The catalyst was filtered off and the filtrate was concentrated 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 (975 mg) was obtained as colorless powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customwas obtained as colorless powder

Sources & evidence

ORD record
ord-bfbc531641b94f088bb8f58effd1d466
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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