Water → HCID 15764275, compound

HRID 990689Notes

Reaction equation

HRID 990689 reaction equation
CO[C:3](=O)[NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:3][NH:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70126049HCID 70126049, compound

Product 1

HCID 15764275HCID 15764275, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Intermediate 6 (0.26 g) in tetrahydrofuran (30 ml) was added lithium aluminium hydride (0.2 g). The reaction was stirred at room temperature for 12 h, before water (0.2 ml), aqueous sodium hydroxide (15%, 0.2 ml) and water (0.6 ml) were added. The precipitates were removed by filtration and the filtrate dried over magnesium sulphate (2 g) and the solvent removed in vacuo. The resulting oil was purified by flash chromatography (silica, eluent 1% methanol/dichloromethane) to yield the title compound as a brown solid (0.07 g).

Workup

  1. additionwere added
  2. customThe precipitates were removed by filtration
  3. dry with materialthe filtrate dried over magnesium sulphate (2 g)
  4. customthe solvent removed in vacuo
  5. customThe resulting oil was purified by flash chromatography (silica, eluent 1% methanol/dichloromethane)

Sources & evidence

ORD record
ord-ab8959985d454782ba6a0384e4269000
Source dataset
uspto-grants-2002_10
Patent number
US06462042B1

Reaction notes

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