Water → HCID 10319686, compound

HRID 1032965Notes

Reaction equation

HRID 1032965 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][C:28]([NH:30][C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=2[OH:38])=O)[CH2:22][CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[CH:7]([N:20]1[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][NH:30][C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=2[OH:38])[CH2:24][CH2:25]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10071310HCID 10071310, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10319686HCID 10319686, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride (606 mg, 16.0 mmol) was added to tetrahydrofuran (25 ml) in several divided portions under ice-cooling, and thereto was added dropwise a solution of the compound (2) (3.43 g, 7.98 mmol) obtained above in tetrahydrofuran (15 ml). The mixture was heated under reflux for 3 hours, and thereto was added water (0.5 ml), 10% sodium hydroxide (0.5 ml) and water (1.0 ml) in that order under ice-cooling. The mixture was stirred at room temperature for 30 minutes. The inorganic substance was removed from the reaction mixture by filtration. The filtrate was dried over anhydrous magnesium sulfate and evaporated to give a yellow-orange glassy substance, which was then purified by column chromatography on silica gel to give a yellow-orange solid. Yield 2.35 g (71%). The thus-obtained solid was recrystallized from ethyl acetate to give colorless needle-like crystals (Compound 14). Yield 987 mg (30%). m.p. 178°-179° C.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. temperaturecooling
  5. customThe inorganic substance was removed from the reaction mixture by filtration
  6. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customto give a yellow-orange glassy substance, which
  9. customwas then purified by column chromatography on silica gel
  10. customto give a yellow-orange solid
  11. customThe thus-obtained solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-31fce42593c04ed7b393e290185f2bf1
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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