Aluminium lithium hydride → HCID 21193235, compound
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]([S:25][C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)([C:20](OCC)=[O:21])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C(OCC)C>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH2:16][C:17]([CH2:20][OH:21])([S:25][C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)[CH2:18][CH2:19]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a slurry of lithium aluminum hydride (0.25 g, 6.6 mmol) in anhydrous diethyl ether (60 mL) at 0° C., a solution of ethyl N-tert-butoxycarbonyl-4-(3-tolylsulfanyl)piperidine-4-carboxylate (2.25 g, 5.9 mmol) in diethyl ether (5 mL) was added dropwise with the temperature of the reacting mixture maintained below 10° C. The resulting mixture was stirred at 0° C. for 1 h., and quenched with successive addition of water (0.25 mL), 15% aqueous NaOH (0.25 mL), and water (10.75 mL). The resultant slurry was stirred at room temp. for one h., and filtered through a small plug of Celite. The filtrate was washed brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the title alcohol.
Workup
- temperaturemaintained below 10° C
- customquenched with successive addition of water (0.25 mL), 15% aqueous NaOH (0.25 mL), and water (10.75 mL)
- stirringThe resultant slurry was stirred at room temp. for one h.
- filtrationfiltered through a small plug of Celite
- washThe filtrate was washed brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-56463cab507847e29c36950a08499261
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06248756B1
Reaction notes
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