Sodium Bicarbonate → 3-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-indol-3-yl]propan-1-ol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si:7]([O:14][CH2:15][CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26][CH2:27][C:28](O)=[O:29])=[CH:18]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C(=O)(O)[O-].[Na+]>C(OCC)C>[Si:7]([O:14][CH2:15][CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26][CH2:27][CH2:28][OH:29])=[CH:18]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of lithium aluminium hydride (0.44 g, 0.011 mol) in diethyl ether (10 mL) was added dropwise at 0° C. solution of 3-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-indol-3-yl]propanoic acid (Intermediate 40; 2 g, 0.011 mol) in ethyl ether (10 mL). The reaction mixture was stirred at room temperature for 45 minutes. Saturated sodium bicarbonate was added into the mixture at 0° C. The organic phase was extracted and the solvent was removed under reduced pressure giving the title compound (3.2 g, 83%), which was used in the next step without further purification.
Workup
- extractionThe organic phase was extracted
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-4b40f4264f2d41a6b16670472e87effa
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233108B2
Reaction notes
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