Tetrahydrofuran → HCID 57554682, compound

HRID 1511900Notes

Reaction equation

HRID 1511900 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[NH2:12][C:13]1([C:33](O)=[O:34])[CH2:17][C:16]([CH3:32])([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:20][CH:19]=2)[O:15][CH2:14]1>CO.C(Cl)Cl>[NH2:12][C:13]1([CH2:33][OH:34])[CH2:17][C:16]([CH3:32])([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:20][CH:19]=2)[O:15][CH2:14]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 57554806HCID 57554806, compound

Product 1

HCID 57554682HCID 57554682, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of lithium aluminum hydride (2.70 ml, 5.40 mmol) (Aldrich) was added carefully to THF (17.99 ml) under nitrogen. 3-amino-5-methyl-5-(4-octylphenyl)tetrahydrofuran-3-carboxylic acid (0.6 g, 1.799 mmol) was added in small portions causing vigorous bubbling. The reaction stirred for about 2 h. TLC in 10% MeOH in methylene chloride showed (Hannessian's stain visualization) reaction complete. The reaction was quenched by addition of water (200 uL) and the reaction stirred about 30 min. 10% NaOH (0.6 mL) was added and the reaction stirred about 30 min. Finally, water (200 uL) was added and the reaction stirred about 30 min. The resulting solid was collected by vacuum filtration and washed with ether. The filtrate was concentrated to a colorless oil. The residue was purified by flash column chromatography (40 g Redi-Sep) eluting with 10-20% methanol in methylene chloride and the product fractions combined. Solvents were removed under reduced pressure. The residue was redissolved in methylene chloride and filtered through a syringe filter into a vial and washed through with methylene chloride. Solvent was removed under reduced pressure to provide (3-amino-5-methyl-5-(4-octylphenyl)tetrahydrofuran-3-yl)methanol (0.192 g, 0.601 mmol, 33.4% yield) as a colorless oil that solidified on standing to a white solid:

Workup

  1. custom(Hannessian's stain visualization) reaction complete
  2. customThe reaction was quenched by addition of water (200 uL)
  3. stirringthe reaction stirred about 30 min
  4. addition10% NaOH (0.6 mL) was added
  5. stirringthe reaction stirred about 30 min
  6. additionFinally, water (200 uL) was added
  7. stirringthe reaction stirred about 30 min
  8. filtrationThe resulting solid was collected by vacuum filtration
  9. washwashed with ether
  10. concentrationThe filtrate was concentrated to a colorless oil
  11. customThe residue was purified by flash column chromatography (40 g Redi-Sep)
  12. washeluting with 10-20% methanol in methylene chloride
  13. customSolvents were removed under reduced pressure
  14. dissolutionThe residue was redissolved in methylene chloride
  15. filtrationfiltered through a syringe
  16. filtrationfilter into a vial and
  17. washwashed through with methylene chloride
  18. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fb7df7b6fbce4d209466d384f330c3c4
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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