Aluminium lithium hydride → HCID 43314999, compound

HRID 1667236Notes

Reaction equation

HRID 1667236 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=O)OC(C)(C)C)[CH2:9][CH2:8]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:14][NH:13][CH:10]1[CH2:9][CH2:8][N:7]([CH2:6][C:5]2[CH:21]=[CH:22][CH:23]=[C:3]([C:2]([F:25])([F:1])[F:24])[CH:4]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 56604362HCID 56604362, compound

Product 1

HCID 43314999HCID 43314999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 1-(3-(trifluoromethyl)benzyl)piperidin-4-ylcarbamate (0.358 g, 1 mmol; Example 41A) in tetrahydrofuran (40 mL) was added LiAlH4 (0.056 g, 1.5 mmol) and the resultant mixture was heated to reflux for 16 hours. Then the reaction mixture was cooled in an ice bath and Na2SO4.10H2O (0.1 g) was added. The mixture was stirred for 1 hour at room temperature, and then the inorganic salts were removed by filtration. The filtrate was evaporated, and the obtained residue was chromatographed on silica gel eluting with 5-10% methanol/dichloromethane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.58 (s, 1H), 7.51 (m, 2H), 7.42 (m, 1H), 5.36 (Bs, 1H), 3.54 (s, 2H), 2.82 (m, 2H), 2.43 (s, 3H), 2.37 (m, 1H), 2.07 (m, 2H), 1.87 (d, J=12.55 Hz, 2H), 1.38 (m, 2H); MS (DCI+) m/z 273 (M+H)+.

Workup

  1. temperatureto reflux for 16 hours
  2. temperatureThen the reaction mixture was cooled in an ice bath
  3. customthe inorganic salts were removed by filtration
  4. customThe filtrate was evaporated
  5. customthe obtained residue was chromatographed on silica gel eluting with 5-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-735fe3fbc72642ce850a5fd86969dcc7
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…