Aluminium lithium hydride → HCID 59004652, compound

HRID 1668454Notes

Reaction equation

HRID 1668454 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][CH2:14][N:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]#[N:25])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1>C(OCC)C>[CH3:7][N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][CH2:14][N:15]1[C:23]2[C:18](=[CH:19][C:20]([CH2:24][NH2:25])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 67339409HCID 67339409, compound

Product 1

HCID 59004652HCID 59004652, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a dry argon purged flask fitted with a magnetic stirbar, condenser and dropping funnel is charged lithium aluminum hydride (80.9 mg, 2.131 mmol), anhydrous diethyl ether (10 mL) and stirring begun. A solution of compound 34 (360 mg, 1.421 mmol) in anhydrous diethyl ether (10 mL) is charged to the dropping funnel and added drop wise to the LiAlH4 suspension and mixture stirred at ambient temperature for 30 minutes. The reaction was quenched by the sequential addition of 100 ul H2O, 125 ul 3M sodium hydroxide and 300 ul H2O. After filtration to remove insolubles, the solution was concentrated and the residue purified twice via chromatography on silica gel (2M NH3 in methanol:CH2Cl2, 5:95 to 1:9) to afford pale yellow oil 36 (149 mg, 40.7%); 1H NMR (DMSO-d6) δ 7.45 (s, 1H), 7.37-7.33 (2×m, 2H), 7.10 (d, 1H, J=8.2 Hz), 6.35 (d, 1H, J=3.1 Hz), 4.15 (t, 2H, J=7.4 Hz), 3.76 (s, 2H), 2.93-2.87 (m, 1H), 2.15 (s, 3H), 2.12-2.03 (m, 1H), 2.00-1.93 (m, 2H), 1.88-1.79 (m, 1H), 1.68-1.52 (m, 3H), 1.44-1.35 (m, 1H); ESI-MS (m/z, %): 258 (M+1, 100%).

Workup

  1. customTo a dry argon purged flask fitted with a magnetic stirbar, condenser
  2. stirringstirred at ambient temperature for 30 minutes
  3. customThe reaction was quenched by the sequential addition of 100 ul H2O, 125 ul 3M sodium hydroxide and 300 ul H2O
  4. filtrationAfter filtration
  5. customto remove insolubles
  6. concentrationthe solution was concentrated
  7. customthe residue purified twice via chromatography on silica gel (2M NH3 in methanol:CH2Cl2, 5:95 to 1:9)

Sources & evidence

ORD record
ord-f19a188789a24de3bb8018b550b22b5a
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

Loading…