Aluminium lithium hydride → HCID 118159705, compound

HRID 628280Notes

Reaction equation

HRID 628280 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[N:12]2[C:13]3[CH:19]=[C:18]([CH3:20])[N:17]([CH2:21][C:22]4[CH:31]=[CH:30][C:25]([C:26](OC)=[O:27])=[CH:24][CH:23]=4)[C:14]=3[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1>C1COCC1>[CH3:7][C:8]1[N:12]2[C:13]3[CH:19]=[C:18]([CH3:20])[N:17]([CH2:21][C:22]4[CH:31]=[CH:30][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=4)[C:14]=3[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118159808HCID 118159808, compound

Product 1

HCID 118159705HCID 118159705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 M LiAlH4 in THF (1.6 mL, 1.6 mmol, Aldrich) was added dropwise to a solution of the crude product of Step 1 in THF (27 mL) at 0° C. After 30 minutes, the reaction was quenched at 0° C. by the dropwise addition of a small amount of water, followed by excess amount of Rochelle's salt. After 10 minutes, sodium sulfate was added and enough DCM to afford a transparent yellow solution. The mixture was then filtered through celite and the solvent was removed in vacuo. Flash chromatography, eluting with a gradient from 0-10% MeOH in DCM afforded product as a light yellow solid (0.11 g, 44% for two steps).

Workup

  1. customthe reaction was quenched at 0° C. by the dropwise addition of a small amount of water
  2. waitAfter 10 minutes
  3. additionsodium sulfate was added
  4. customenough DCM to afford a transparent yellow solution
  5. filtrationThe mixture was then filtered through celite
  6. customthe solvent was removed in vacuo
  7. washFlash chromatography, eluting with a gradient from 0-10% MeOH in DCM afforded product as a light yellow solid (0.11 g, 44% for two steps)

Sources & evidence

ORD record
ord-9b815e79fc3b4992b69595c852219c3e
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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