Water → HCID 15359283, compound

HRID 1925521Notes

Reaction equation

HRID 1925521 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[CH2:17][C:18](OC)=[O:19])[CH2:14]2.O.[OH-].[Na+]>O1CCCC1>[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[CH2:17][CH2:18][OH:19])[CH2:14]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54117306Methyl 2-adamantylacetate

Product 1

HCID 15359283HCID 15359283, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminium hydride (1.58 g, 41.63 mmol) in anhydrous tetrahydrofuran was slowly added a solution of Intermediate 72 (6.2 g, 29.76 mmol) in tetrahydrofuran (55 mL). The reaction mixture was stirred at room temperature overnight. Then water (12 mL), sodium hydroxide 4N (12 mL) and finally water again (36 mL) were added into the solution at 0° C. The mixture was stirred for some minutes and the resulting salts were filtered through a pad of Celite® washing with ethyl acetate (100 mL). The crude was treated with water and methylen chloride and the solvent of the organic layer was removed under reduced pressure to give the title compound as an oil (4.83 g, 90%), which was used in the next step without further purification.

Workup

  1. stirringThe mixture was stirred for some minutes
  2. filtrationthe resulting salts were filtered through a pad of Celite®
  3. washwashing with ethyl acetate (100 mL)
  4. additionThe crude was treated with water and methylen chloride
  5. customthe solvent of the organic layer was removed under reduced pressure

Sources & evidence

ORD record
ord-f6ef2fa6d30e4b5592c314d2f8cb18a7
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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