HCID 11547510, compound → HCID 11532855, compound

HRID 2242591Notes

Reaction equation

HRID 2242591 reaction equation
[CH3:1][C:2]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][C:30]([NH:32][CH2:33][CH3:34])=[O:31])[CH:23]=2)=[C:18]([OH:35])[CH:17]=1)([CH3:15])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:33]([NH:32][C:30]([NH:29][CH2:28][C:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:2]([CH3:15])([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[CH3:1])=[CH:17][C:18]=2[OH:35])[CH:27]=[CH:26][CH:25]=1)=[O:31])[CH3:34]

Participants

4

Reactant 2

HCID 11547510HCID 11547510, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11532855HCID 11532855, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 20 (0.2 g, 0.416 mmol, 1.0 eq) in tetrahydrofuran (10 mL) under nitrogen atmosphere at 0° C. was added lithium aluminum hydride (1.0 M in THF, 1.6 mL, 1.60 mmol, 4.0 eq). The mixture was slowly warmed up to room temperature over 2.5 hours, and LC/MS showed the reaction was complete. The reaction was quenched with ice chips, and then water/ethyl acetate was 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 (neutral aluminum gel, 2% methanol in dichloromethane).

Workup

  1. customThe reaction was quenched with ice chips
  2. additionwater/ethyl acetate was 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
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography (neutral aluminum gel, 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1cf87582fd524c2683585ce0027cd8c6
Source dataset
uspto-grants-2010_03
Patent number
US07671052B2

Reaction notes

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