Tert-butyl 4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)prop-2-ynyl]piperidine-1-carboxylate → tert-butyl (Z)-4-(3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)allyl)piperidine-1-carboxylate
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[CH2:8][O:9][C:5]=2[C:4]=1[C:13]#[C:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[CH2:8][O:9][C:5]=2[C:4]=1/[CH:13]=[CH:14]\[CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of tert-butyl 4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)prop-2-ynyl]piperidine-1-carboxylate (0.0775 g, 0.201 mmol) synthesized in Example B58, Step 2 in ethanol (5 mL) was added with 5% palladium/carbon (wetted with 50% water, 0.0800 g), and the mixture was stirred overnight at room temperature under a hydrogen atmosphere. The reaction mixture was filtered through Celite, the resulting filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl (Z)-4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)allyl]piperidine-1-carboxylate (0.0671 g, 86%).
Workup
- filtrationThe reaction mixture was filtered through Celite
- concentrationthe resulting filtrate was concentrated
- customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-3f3a47f773c44b2db92fed9243cf74b5
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156827B2
Reaction notes
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