HCID 11619385, compound → HCID 11669341, compound

HRID 2242592Notes

Reaction equation

HRID 2242592 reaction equation
[CH2:1]([NH:3][C:4](=[O:33])[NH:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:31])([CH3:30])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=O)[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:15][C:14]=2[OH:32])[CH:10]=[CH:11][CH:12]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([NH:3][C:4]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:31])([CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:30])=[CH:15][C:14]=2[OH:32])[CH:10]=[CH:11][CH:12]=1)=[O:33])[CH3:2]

Participants

4

Reactant 2

HCID 11619385HCID 11619385, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11669341HCID 11669341, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 35 (0.1 g, 0.22 mmol, 1.0 eq) in tetrahydrofuran (10 mL) under nitrogen at 0° C. was added lithium aluminum hydride (1.0 M in THF, 1.76 mL, 1.76 mmol, 4.0 eq). The mixture was slowly warmed up to room temperature over 2.5 hours. The reaction was quenched with ice chips, and then water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate (2×20 mL), and the combined organic layer was washed with water (20 mL), brine (20 mL) and dried over anhydrous MgSO4 The solvent was removed under reduced pressure, and the residue was purified by column chromatography (silica gel, 2-10% methanol in dichloromethane).

Workup

  1. customThe reaction was quenched with ice chips
  2. additionwater and ethyl acetate were added
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  4. washthe combined organic layer was washed with water (20 mL), brine (20 mL)
  5. dry with materialdried over anhydrous MgSO4 The solvent
  6. customwas removed under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel, 2-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-060f3dff03094b59a171010c50b3dbc2
Source dataset
uspto-grants-2010_03
Patent number
US07671052B2

Reaction notes

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