Lithium Hydroxide → 4-(1-(Naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoic acid
Reaction equation
[C:1]1([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][CH2:21][CH2:22][C:23]([O:25]C)=[O:24])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Li+]>CO.O>[C:1]1([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
Procedure
To a solution of Methyl 4-(1-(naphthalene-1-ylsulfonyl)piperidin-2-yl)butanoate (Ester-21) (4.95 g, 13.18 mmol.) in Methanol/Water (54 ml/36 ml) Lithium hydroxide (1.58 g, 65.9 mmol) was added and the reaction mixture was stirred over night at room temperature. The completion of the reaction was controlled via Thin-layer chromatography. After completion the Methanol was evaporated in vacuum, and the residue was triturated with Ethylacetate. The mixture was made acidic with diluted HCl. The aqueous layer was extracted 2× with Ethylacetate, the combined organic layers were dried over Sodium sulfate and were evaporated in vacuum to give the desired Product 4-(1-(Naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoic acid (S-21) (4.38 g, 91%).
Workup
- customAfter completion the Methanol was evaporated in vacuum
- customthe residue was triturated with Ethylacetate
- extractionThe aqueous layer was extracted 2× with Ethylacetate
- dry with materialthe combined organic layers were dried over Sodium sulfate
- customwere evaporated in vacuum
Sources & evidence
- ORD record
- ord-57b1f3daf1994f0fa50636de1cf01f7a
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124624B2
Reaction notes
Loading…