Aluminium lithium hydride → HCID 58134720, compound

HRID 444769Notes

Reaction equation

HRID 444769 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([NH:15][C:16]1([CH2:20][C:21](OCC)=[O:22])[CH2:19][CH2:18][CH2:17]1)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1.O.C(OCC)(=O)C>[CH2:7]([NH:15][C:16]1([CH2:20][CH2:21][OH:22])[CH2:19][CH2:18][CH2:17]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58134741HCID 58134741, compound

Product 1

HCID 58134720HCID 58134720, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

LiAlH4 (3.88 g, 0.102 mol) was added to a solution of ethyl 1-(benzoylamino)-cyclobutylacetate (5.30 g, 20.3 mmol) in THF (100 mL) at room temperature. The mixture was stirred for 1 hour, then refluxed for one additional hour. The mixture was cooled in an ice-water bath, a few drops of water were added, and the mixture was allowed to stand overnight. The mixture was diluted with ethyl acetate, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Distillation of the residue gave the title compound as a colorless oil (2.53 g, 61%). 1H-NMR (400 MHz, CDCl3) δ 1.69-1.86 (2H, m), 1.88 (2H, t, J=5.5 Hz), 1.92-2.09 (4H, m), 3.73 (2H, s), 3.87 (2H, t, J=5.5 Hz), 7.22-7.35 (5H, m).

Workup

  1. temperaturerefluxed for one additional hour
  2. temperatureThe mixture was cooled in an ice-water bath
  3. waitto stand overnight
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-8e615e996ba94d81a513904c0199882a
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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