Water → HCID 13491247, compound

HRID 1719620Notes

Reaction equation

HRID 1719620 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.Cl.[NH2:10][CH:11]1[CH:18]2[C:19](=[O:27])[C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=3[C:12]1([CH3:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2.O>O1CCCC1>[NH2:10][CH:11]1[CH:18]2[CH:19]([OH:27])[C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=3[C:12]1([CH3:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2

Participants

5

Reactant 3

HCID 962WaterHCID 20267368HCID 20267368, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 13491247HCID 13491247, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension 2 g. of lithium aluminum hydride (LAH) in 250 mL of tetrahydrofuran (THF) was added a slurry of 1 g. (0.003 mole) of 13-amino-6,7,8,9,10,11-hexahydro-3-hydroxy-5-methyl-5,11-methanobenzocyclodecen-12(5H)-one hydrochloride dihydrate in 50 mL of THF over a period of 1 hour. The reaction mixture was refluxed for 25 hours and then cooled and excess LAH was decomposed by careful addition of 2 mL of water. The reaction mixture was filtered and the filtrate washed with aqueous ammonium chloride, dried (anhydrous Na2SO4) and evaporated under reduced pressure to afford a white residue which was recrystallized from acetone-ethanol (5:1) to afford 500 mg (68% yield) of the title compound, mp 232°-235° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 25 hours
  2. temperaturecooled
  3. filtrationThe reaction mixture was filtered
  4. washthe filtrate washed with aqueous ammonium chloride
  5. dry with materialdried (anhydrous Na2SO4)
  6. customevaporated under reduced pressure
  7. customto afford a white residue which
  8. customwas recrystallized from acetone-ethanol (5:1)

Sources & evidence

ORD record
ord-d2cc70e97b574be08cf5682214a36ef2
Source dataset
uspto-grants-1985_09
Patent number
US04540806

Reaction notes

Loading…