Hydrogen chloride-ethyl acetate → HCID 86678702, compound

HRID 1620509Notes

Reaction equation

HRID 1620509 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:10][CH:9]2[CH2:11][CH:5]([CH2:6][N:7](C(OC(C)(C)C)=O)[CH2:8]2)[CH2:4]1.[ClH:19].C(OCC)(=O)C>CO>[ClH:19].[CH:9]12[CH2:11][CH:5]([CH2:4][CH:3]([CH2:2][OH:1])[CH2:10]1)[CH2:6][NH:7][CH2:8]2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86678701HCID 86678701, compound

Product 1

HCID 86678702HCID 86678702, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-tert-butyl 7-hydroxymethyl-3-azabicyclo[3.3.1]nonane-3-carboxylate (7.78 g) in methanol (76 mL) was added 4M hydrogen chloride/ethyl acetate solution (76 mL). The reaction mixture was stirred at room temperature for 4 hr, and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (50 mL), and Amberlyst A-21 was added. The mixture was stirred at room temperature for 20 min, and the solid was removed by filtration. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol/ethyl acetate to give the title compound (5.22 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (50 mL)
  3. additionAmberlyst A-21 was added
  4. stirringThe mixture was stirred at room temperature for 20 min
  5. customthe solid was removed by filtration
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was recrystallized from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-189db74387ae42bab70b3163274221e0
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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