Water → HCID 70008253, compound

HRID 1267892Notes

Reaction equation

HRID 1267892 reaction equation
[CH2:1]([N:8]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C@@H:9]1[CH2:15][CH2:14][C@@H:13]2[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@:10]1([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:11][C@H:12]2[C:24](O)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:33]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]1[CH2:15][CH2:14][C@@H:13]2[N:16]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C@@:10]1([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:11][C@H:12]2[CH2:24][OH:25])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 70008428HCID 70008428, compound

Product 1

HCID 70008253HCID 70008253, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1R*,2R*,5S*,6R*)-2-Dibenzylamino-8-benzyl-6-(hydroxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Description 21; 400 mg, 0.78 mmol) was dissolved in tetrahydroftiran (10 mL) and treated with lithium aluminium hydride solution (800 μL, 1M, 0.8 mmol) in tetrahydrofuran. The resulting mixture was stirred for 16 hours, then a further portion of lithium aluminium hydride solution (200 μL, 1M, 0.8 mmol) in tetrahydrofuran was added. Stirred at 50° C. for 1 hour, then cooled, and water (40 μL) added, followed by 15% aqueous sodium hydroxide solution (40 μL), then water (120 μL). The suspension formed was filtered and the filtrate taken up in water (10 mL). This mixture was extracted with ethyl acetate (2×10 mL) and the extracts were dried (MgSO4), before being concentrated in vacuo. The gum remaining was purified by silica chromatography to give the title compound (295 mg, 0.59 mmol) as a gum.

Workup

  1. stirringStirred at 50° C. for 1 hour
  2. temperaturecooled
  3. customThe suspension formed
  4. filtrationwas filtered
  5. extractionThis mixture was extracted with ethyl acetate (2×10 mL)
  6. dry with materialthe extracts were dried (MgSO4)
  7. concentrationbefore being concentrated in vacuo
  8. customThe gum remaining was purified by silica chromatography

Sources & evidence

ORD record
ord-c2d52ffb93f74f60a37949e4a2c6088e
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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