Aluminium lithium hydride → HCID 86616400, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:20](OC)=[O:21])[C:17]2[C:12](=[C:13]([F:19])[CH:14]=[C:15]([F:18])[CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[C:17]2[C:12]=1[CH2:11][CH2:10][C:9]2([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:20][OH:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of methyl 1-[(tert-butoxycarbonyl)amino]-4,6-difluoroindane-1-carboxylate from Step D (2.80 g, 8.55 mmol) in THF (30 mL) at −78° C. was added LiAlH4 (18.0 mL of a 1 M solution in THF, 18.0 mmol), dropwise, over 30 min. The reaction mixture was stirred at −78° C. for 2 h, then quenched with H2O (1 mL), then 1 N aqueous NaOH (2 mL), then H2O (2 mL), then EtOAc (2 mL). The reaction mixture was warmed to ambient temperature, saturated aqueous NaHCO3 (150 mL) was added, and the mixture was extracted with EtOAc (200 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50, to give the title compound. MS: m/z=244 (M−C4H7).
Workup
- customquenched with H2O (1 mL)
- temperatureThe reaction mixture was warmed to ambient temperature
- additionsaturated aqueous NaHCO3 (150 mL) was added
- extractionthe mixture was extracted with EtOAc (200 mL)
- extractionThe organic extract
- dry with materialwas dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by silica gel chromatography
- washeluting with a gradient of hexane
Sources & evidence
- ORD record
- ord-23898f44f50f4e0aa78ca9fcecd5d6cd
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893079B2
Reaction notes
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