Aluminium lithium hydride → HCID 22141153, compound

HRID 428932Notes

Reaction equation

HRID 428932 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:10]1[CH2:15][CH:14]2[CH:12]([C:13]2([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=2)[CH3:16])[C:11]1=O)[CH:8]=[CH2:9]>O1CCCC1>[CH2:7]([N:10]1[CH2:11][CH:12]2[CH:14]([C:13]2([C:17]2[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=2)[NH2:23])[CH3:16])[CH2:15]1)[CH:8]=[CH2:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22141140HCID 22141140, compound

Product 1

HCID 22141153HCID 22141153, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To dry tetrahydrofuran (300 ml) under nitrogen was added dropwise lithium aluminium hydride (1M in tetrahydrofuran, 75 ml, 75 mmol). To this solution, 3-allyl-6-(3-aminophenyl)-6-methyl-3-azabicyclo[3.1.0]hexan-2-one (Preparation 51, 9.0 g, 37.1 mmol) dissolved in tetrahydrofuran (200 ml), was added dropwise at 0° C. The reaction mixture was stirred for 1 h and then heated to 50° C. for 3 h. The reaction mixture was quenched with water (150 ml) and solid sodium hydrogen carbonate was added. The slurry was extracted with ethyl acetate and then dichloromethane. The organic extracts were combined and dried (Na2SO4) and then concentrated in vacuo to give the title compound as a thick yellow oil (8.5 g, 100%).

Workup

  1. additionwas added dropwise at 0° C
  2. customThe reaction mixture was quenched with water (150 ml) and solid sodium hydrogen carbonate
  3. additionwas added
  4. extractionThe slurry was extracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-053dd7edbd0e43cbb54dc75b39ca87c6
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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