Aluminium lithium hydride → HCID 22571123, compound

HRID 1372415Notes

Reaction equation

HRID 1372415 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:28])[CH2:16][C:15]2[NH:14][CH:13]=[C:12]([CH2:17][CH2:18][C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=O)[C:11]=2[C:10](=O)[CH2:9]1>O1CCCC1.[OH-].[Na+]>[CH3:7][C:8]1([CH3:28])[CH2:16][C:15]2[NH:14][CH:13]=[C:12]([CH2:17][CH2:18][CH2:19][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:11]=2[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22571117HCID 22571117, compound

Product 1

HCID 22571123HCID 22571123, compoundYield 13.5%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 1.1 g (30 mmol) of lithium aluminum hydride in 10 mL of tetrahydrofuran was added dropwise a solution of 1.8 g (43 mmol) of 6,6-dimethyl-3-(3-morpholin-4-yl-3-oxo-propyl)-1,5,6,7-tetrahydro-indol-4-one in 10 mL of tetrahydrofuran. The mixture was stirred at 80° C. for 2.5 hours and then cooled in an ice bath. Ice cubes were added to the reaction mixture slowly until no more gas was generated. A few drops of 2 N sodium hydroxide were added and the reaction mixture was stirred at room temperature for 30 minutes, extracted with ethyl acetate, and the extract dried over anhydrous sodium sulfate and concentrated to give 1.6 g of 6,6-dimethyl-3-(3-morpholin-4-yl-propyl)-4,5,6,7-tetrahydro-1H-indole as a white solid which was used without further purification. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 9.75 (br s, 1H, NH), 6.24 (s, 1H), 3.54 (m, 4H, 2×CH2), 2.23–2.31 (m, 12H, 6×CH2), 1.58 (m, 2H, CH2), 1.40 (m, 2H, CH2), 0.92 (s, 6H, 2×CH3). MS m/z 276 [M+].

Workup

  1. temperaturecooled in an ice bath
  2. additionIce cubes were added to the reaction mixture slowly until no more gas
  3. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  4. extractionextracted with ethyl acetate
  5. dry with materialthe extract dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ab8ca413a50e44d58634fa60a96b9f7d
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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