Diisobutylaluminum hydride → 2-[(3-Chloro-4-fluorophenyl)amino]propan-1-ol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C@H:10]([C:12](OC)=[O:13])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].CC(C[AlH]CC(C)C)C.[NH4+].[Cl-].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([CH3:11])[CH2:12][OH:13])[CH:5]=[CH:6][C:7]=1[F:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
Methyl N-(3-chloro-4-fluorophenyl)alaninate (1-3, 0.774 g, 3.341 mmol) was treated with DIBAL (6.682 mL, 6.682 mmol) in anhydrous THF (100 mL) at −78° C. The resulting solution was warmed to 25° C. while stirring over 1 h. The resulting solution was treated with a saturated aqueous solution of NH4Cl (1.0 mL) and ether (300 mL) then allowed to stir 30 min. MgSO4 was added and stirred for 20 min then reaction mixture was filtered. The filtrate was concentrated under vacuum to yield 2-[(3-chloro-4-fluorophenyl)amino]propan-1-ol (1-4). 1H NMR (300 MHz, CDCl3) δ 7.26 (s, 1H), 6.94 (dd, J=8.8, 8.8 Hz, 1H), 6.67 (dd, J=6.1, 3.0 Hz, 1H), 6.49 (dd, J=8.8, 5.8, 3.0 Hz, 1H), 3.74 (m, 1H), 3.55 (m, 2H), 1.19 (d, J=6.1 Hz, 3 H). MS 204.2 found, 204.6 (M+H+) required.
Workup
- stirringto stir 30 min
- stirringstirred for 20 min
- customreaction mixture
- filtrationwas filtered
- concentrationThe filtrate was concentrated under vacuum
Sources & evidence
- ORD record
- ord-c66453339ad34c13b67562c6c227f6d4
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608739B2
Reaction notes
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