Aluminium lithium hydride → HCID 90003553, compound
Reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@H:12]([NH:14][C:15](=O)[CH2:16][CH2:17][C@H:18]2[CH2:27][C:26](=[O:28])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19]2)[CH3:13])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCOCC1>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@H:12]([NH:14][CH2:15][CH2:16][CH2:17][C@@H:18]2[CH2:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:26]([OH:28])[CH2:27]2)[CH3:13])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
N—((R)-1-(4-Fluoronaphthalen-1-yl)ethyl)-3-((R)-4-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide (830 mg, 2.131 mmol) was added to a suspension of LAH (162 mg, 4.26 mmol) in dioxane (15 mL) at 0° C. The reaction mixture was stirred for 30 minutes at 25° C. and heated at 100° C. and further maintained for 12 h. The mixture was allowed to RT, cooled to 0° C. and slowly quenched with ethyl acetate (5 mL) followed by water (5 mL). Reaction mixture was extracted with ethyl acetate (30 mL), washed with brine solution (20 mL) and dried over Na2SO4 and concentrated to get crude compound which was used as it is in next reaction; m/z 378.6.
Workup
- temperatureheated at 100° C.
- temperaturefurther maintained for 12 h
- customwas allowed to RT
- temperaturecooled to 0° C.
- customslowly quenched with ethyl acetate (5 mL)
- customReaction mixture
- extractionwas extracted with ethyl acetate (30 mL)
- washwashed with brine solution (20 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customto get crude compound which
- customis in next reaction
Sources & evidence
- ORD record
- ord-09505deecac94be0af6f1f61a0ca8f82
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227919B2
Reaction notes
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