Aluminium lithium hydride → 3-Aminomethyl-5-fluoromethylbenzylalcohol
Reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH2:15][F:16])[CH:14]=1)[C:8](OC)=[O:9])=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH2:15][F:16])[CH:14]=1)[CH2:8][OH:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl 3-azidomethyl-5-fluoromethylbenzoate (35) (476 mg, 2.13 mmol) was dissolved in THF (21.3 mL). The air was evacuated from the reaction system, and then Ar was charged therein. In another recovery flask filled with Ar, LiAlH4 (408 mg, 10.7 mmol) was placed. To this was added THF (21.3 mL) with ice-cooling to give a suspension. To the suspension was added dropwise the solution of the compound (35), and stirred for 2 hours at 0° C. TLC was used to confirm there was no starting material in the mixture. Then, the reaction was quenched with MeOH (10 mL). The mixture was filtered through cerite to remove metals. The filtrate was evaporated under reduced pressure. The residue was purified by neutral silica gel column chromatography (hexane:EtOAc=1:1, then EtOAc:MeOH=2:1) to isolate 3-aminomethyl-5-fluoromethylbenzylalcohol (38) (172 mg, 48%) as a yellow solid.
Workup
- customThe air was evacuated from the reaction system
- additionAr was charged
- temperaturecooling
- customto give a suspension
- customThen, the reaction was quenched with MeOH (10 mL)
- filtrationThe mixture was filtered through cerite
- customto remove metals
- customThe filtrate was evaporated under reduced pressure
- customThe residue was purified by neutral silica gel column chromatography (hexane
Sources & evidence
- ORD record
- ord-4dfb9da26e904d4fb5444bc8adfc1575
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633304B2
Reaction notes
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