Allyl bromide → 1-(2-Propenyl)-4-tert-butyloxycarbonyl-2-piperazinone

HRID 1432938Notes

Reaction equation

HRID 1432938 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15](Br)[CH:16]=[CH2:17]>C1COCC1>[CH2:17]([N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]1=[O:14])[CH:16]=[CH2:15]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 544523841-(2-Propenyl)-4-tert-butyloxycarbonyl-2-piperazinoneYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(tert-Butyloxycarbonyl)-piperazin-2-one (1.0 g, 5.0 mmol), EXAMPLE 40, is alkylated with allyl bromide (0.48 ml, 5.5 mmol) in THF (20 ml) using the procedure described in Example 92, Part A. The title compound (0.92 g, 3.8 mmol) is obtained as a colorless liquid after chromatographed (50% ethyl acetate/hexane). EI MS m/z 240 (M+); 1H NMR (CDCl3, 300 MHz) δ5.80-5.68 (m, 1H), 5.23-5.15 (m, 2H), 4.09 (s, 2H), 4.03 (d, 2H), 3.63 (t, 2H), 3,30 (t, 2H), 1.45 (s, 9H).

Sources & evidence

ORD record
ord-281777f1be8248fd9c08489322caa3c7
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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