Methanol → Tert-butyl 4-[(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.CO.[C:28]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>C1COCC1>[CH3:28][O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.400 g, 1.15 mmol) obtained in Example A16, Step 1, methanol (0.0442 g, 1.38 mmol) and triphenylphosphine (0.454 g, 1.73 mmol) in THF (8 mL) was added with a solution of a 40% solution of diethyl azodicarboxylate in toluene (0.901 g, 2.07 mmol) in THF (2 mL), and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/ethyl acetate) to obtain tert-butyl 4-[(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.107 g, 25%).
Workup
- concentrationThe reaction mixture was concentrated
- customthe resulting residue was purified by silica gel column chromatography (chloroform/ethyl acetate)
Sources & evidence
- ORD record
- ord-3fae58a6bc334b1f92c7c101f1c07f7f
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156827B2
Reaction notes
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