Aluminium lithium hydride → HCID 58721947, compound

HRID 901060Notes

Reaction equation

HRID 901060 reaction equation
[CH2:1]([C:3]1([CH2:18][C:19]([NH2:21])=O)[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([C:3]1([CH2:18][CH:19]=[NH:21])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 21907570HCID 21907570, compound

Product 1

HCID 58721947HCID 58721947, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of compound 6 (119 mg, 0.42 mmol) in dry THF (3 mL) was added dropwise to 1M LiAlH4 in THF (624 μL, 0.62 mmol, 1.5 eq) and stirred for two hours at room temperature under argon. Another equivalent of 1M LiAlH4 in THF (420 μL, 0.42 mmol, 1.0 eq) was then added and the reaction was stirred overnight. The resulting mixture was then slowly quenched with EtOAc and poured over water to form an emulsion. The emulsion was filtered, and the aqueous layer was separated and extracted twice with EtOAc. The three organic phases were then combined, dried with Na2SO4, concentrated, and purified by column chromatography using 50:50:EtOAc:Hexane to give a yellow-brown solid (40 mg, 36%): mp 101-103° C. 1HNMR (CDCl3, δ TMS): 0.94 (t, 3H), 1.38 (t, 3H), 1.96 (m, 2H), 2.73 (qd, 2H), 2.87 (q, 2H), 2.99 (t, 2H), 3.32 (m, 1H, CH═N), 3.87 (t, 2H), 7.04-7.43 (m, 3H, Ar—H), 7.89 (br, 1H, NH). MS+: m/z 293 (MNa+), 271 (MH+). MS−: m/z 269 ([M−H]−). Anal. (C17H22N2O.0.5H2O): C, H, N.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe resulting mixture was then slowly quenched with EtOAc
  3. additionpoured over water
  4. customto form an emulsion
  5. filtrationThe emulsion was filtered
  6. customthe aqueous layer was separated
  7. extractionextracted twice with EtOAc
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-611c3f4121854a13bf1d9a27bcbbb2bf
Source dataset
uspto-grants-2008_04
Patent number
US07361680B2

Reaction notes

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