Benzylamine → HCID 70007537, compound

HRID 1267890Notes

Reaction equation

HRID 1267890 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@:9]1([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:10](=O)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([BH3-])#N.[Na+]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:30]([NH:37][C@@H:10]1[CH2:11][CH2:12][C@@H:13]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@:9]1([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:15][C@H:14]2[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 69889518(1R*,5S*,6R*)-8-Benzyl-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octan-2-one

Product 1

HCID 70007537HCID 70007537, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

(1R*,5S*,6R*)-8-Benzyl-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octan-2-one (Description 17; 5.0 g, 12.8 mmol), p-toluenesulfonic acid monohydrate (25 mg) and benzylamine (2.1 g, 20 mmol) in toluene (50mL) was heated at reflux under Dean Stark conditions for 24 hours, then cooled and the solvent removed in vacuo. The residue was dissolved in methanol (100 mL) and sodium cyanoborohydride (900 mg, 14 mmol) added. The solution formed was stirred at room temperature for 2 hours then concentrated to approximately ¼ volume. Water (500 mL) was added and the suspension formed was extracted with ethyl acetate (2×500 mL). The extracts were dried (MgSO4) and concentrated, before the residue was purified by silica chromatography to give the title compound (3.87 g, 8 mmol) as a gum.

Workup

  1. temperatureat reflux under Dean Stark conditions for 24 hours
  2. temperaturecooled
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in methanol (100 mL)
  5. customThe solution formed
  6. concentrationthen concentrated to approximately ¼ volume
  7. additionWater (500 mL) was added
  8. customthe suspension formed
  9. extractionwas extracted with ethyl acetate (2×500 mL)
  10. dry with materialThe extracts were dried (MgSO4)
  11. concentrationconcentrated, before the residue
  12. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-313781dab4784a6c9ec4779da0e9b438
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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