Hydrochloric Acid → (1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

HRID 2088128Notes

Reaction equation

HRID 2088128 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[CH2:14][CH2:15][C@@:9]1([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@H:10]([O:16][Si](CC)(CC)CC)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([N:8]1[C@@H:13]2[CH2:14][CH2:15][C@@:9]1([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@H:10]([OH:16])[CH2:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69889465(1R,2R,5R)-8-Benzyl-1-phenyl-2-triethylsilyloxy-8-azabicyclo[3.2.1]octane

Product 1

HCID 69688994(1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-olYield 103.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (1R,2R,5R)-8-benzyl-1-phenyl-2-triethylsilyloxy-8-azabicyclo[3.2.1]octane (Description 52; 107 mg, 0.26 mmol), 2M hydrochloric acid (3 ml) and methanol (6 ml) was stirred at +55° C. for 15 minutes, then concentrated in vacuo and quenched with saturated aqueous NaHCO3. The mixture was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated to give the title compound (79 mg, 96%).

Workup

  1. concentrationconcentrated in vacuo
  2. customquenched with saturated aqueous NaHCO3
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5f68bde183be42919f6aa0c26159c787
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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