Tetrahydrofuran → HCID 23121930, compound
Reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH:9]2C(OCC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:26]1([Mg]Br)[CH2:28][CH2:27]1.[Cl-].[NH4+].[O:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[C:15]1([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:13][CH:12]2[C:37]([CH:26]2[CH2:28][CH2:27]2)([CH:36]2[CH2:34][CH2:35]2)[OH:33])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
Procedure
To a solution of ethyl 1,4-bis(phenylmethyl)-2-piperazine carboxylate (5.0 g, 15 mmol) in tetrahydrofuran (70 mL) was added dropwise over 20 minutes a 0.5 M solution of cyclopropylmagnesium bromide in tetrahydrofuran (100 mL, 50 mmol) with ice cooling, and the mixture was stirred for 30 minutes with ice cooling. After further stirring at room temperature overnight, to the reaction solution was added an aqueous saturated ammonium chloride solution (300 mL), and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=15:1) to obtain the title compound (1.3 g, yield 24%).
Workup
- stirringAfter further stirring at room temperature overnight, to the reaction solution
- extractionthe resulting mixture was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=15:1)
Sources & evidence
- ORD record
- ord-35ef84b929f24c6bbcb0f16bec281ed2
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795267B2
Reaction notes
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