Water → (3-{(R*)-1-[(S)-1-(2,3-Dihydrobenzo[1,4]dioxin-2-yl)methyl]piperidin-3-yl}phenyl)methanol
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([C@@H:18]3[O:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[O:20][CH2:19]3)=O)[CH2:11]2)[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[O:23]1[C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[O:20][CH2:19][C@@H:18]1[CH2:16][N:12]1[CH2:13][CH2:14][CH2:15][C@H:10]([C:6]2[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][CH:7]=2)[CH2:11]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
((R*)-3-[1-((R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)piperidin-3-yl]benzoic acid methyl ester (54 mg, 0.147 mmol) was dissolved in dry THF (4 ml) and cooled to 0° C. LiAlH4 (26 mg, 0.680 mmol) was added and the mixture was stirred at RT for 2 h. Water (1 ml), 1 M NaOH (1 ml) and again water (1 ml) were added slowly. The mixture was filtered through Celite and evaporated. Flash chromatography, using a gradient of heptane/EtOAc, gave 3.5 mg of the title compound.
Workup
- filtrationThe mixture was filtered through Celite
- customevaporated
Sources & evidence
- ORD record
- ord-6c24d14468ef4f1cbe05d5a9154f7157
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492549B2
Reaction notes
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