Aluminium lithium hydride → HCID 9879361, compound

HRID 722828Notes

Reaction equation

HRID 722828 reaction equation
[CH3:1][C@H:2]1[C@@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[O:5][C:4](=O)[NH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][NH:3][C@H:2]([C@H:6]([OH:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH3:1]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 57234797HCID 57234797, compound

Product 1

HCID 9879361HCID 9879361, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of 107 (160 mg, 0.52 mmol) in THF(20 mL), LiAlH4 (1M in THF, 1.04 mL, 1.04 mmol), was added dropwise. The mixture was stirred overnight at room temperature. A further portion of LiAlH4 (1.04 mL, 1.04 mmol) was added and the reaction left for 2 more days. The reaction was quenched with H2O containing a few drops of NH4OH (20 mL) and extracted with EtOAc (3×20 mL). The combined extracts were successively washed with. H2O (30 mL) and brine (30 mL), dried over Na2SO4 and concentrated in vacuo. The crude was purified by column chromatography on silica (50% to 75% CH2Cl2/hexane to 100% CH2Cl2 to 10% MeOH/CHCl3 and a few drops of NH4OH) to give 108 as a white solid (35 mg, 23% yield).

Workup

  1. waitthe reaction left for 2 more days
  2. customThe reaction was quenched with H2O containing a few drops of NH4OH (20 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe combined extracts were successively washed with
  5. dry with materialH2O (30 mL) and brine (30 mL), dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by column chromatography on silica (50% to 75% CH2Cl2/hexane to 100% CH2Cl2 to 10% MeOH/CHCl3 and a few drops of NH4OH)

Sources & evidence

ORD record
ord-e4541e8634b94bd380ed3e1d79a9b15b
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

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