Aluminium lithium hydride → 2-Benzyloxy-5-trifluoromethyl-benzylamine

HRID 392909Notes

Reaction equation

HRID 392909 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:16]=1[CH2:17][N:18]=[N+]=[N-])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH2:7]([O:14][C:15]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][C:16]=1[CH2:17][NH2:18])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 226619412-Benzyloxy-5-trifluoromethyl-benzylazide

Product 1

HCID 226618432-Benzyloxy-5-trifluoromethyl-benzylamineYield 82%

Procedure

LAH (136 mg, 3.58 mmol) was added to a solution of 2-benzyloxy-5-trifluoromethyl-benzylazide (1.1 g, 3.58 mmol) at 0° C. After 1 hour, the reaction was quenched by the sequential addition of water (136 μL), 15% NaOH (136 μL), and water (400 μL), the mixture was diluted with dichloromethane and dried with MgSO4, filtered and concentrated. The residue was purified by flash chromatography (3% methanol/dichloromethane) to afford 825 mg (82%) of the title compound as a colorless oil. MS 282 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.6-7.3 (m, 7H); 6.92 (d, 1H, J=9.1 Hz); 5.18 (s, 2H); 3.9 (s, 2H); 2.65 (bs, 2H).

Workup

  1. customthe reaction was quenched by the sequential addition of water (136 μL), 15% NaOH (136 μL), and water (400 μL)
  2. additionthe mixture was diluted with dichloromethane
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-3fbdc7e0cfbb47b19bf7c027a0127a45
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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