Sodium Iodide → HCID 18461084, compound

HRID 2409931Notes

Reaction equation

HRID 2409931 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[C:10]([OH:20])=[C:11](C(OC)=O)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-]>N1C=CC=CC=1>[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[C:10](=[O:20])[CH2:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 71226774HCID 71226774, compound

Product 1

HCID 18461084HCID 18461084, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 8-benzyl-2-hydroxy-8-azabicyclo[3.2.1]oct-2-ene-3-carboxylate (68 mg, 0.249 mmol) in pyridine (2.5 ml) was added NaI (746 mg, 4.98 mmol). The reaction mixture was then reflux at 120° C. for 7.5 hr. The reaction mixture was concentrated and placed under vacuum. The residue was then partitioned between EtOAc and water. The aqueous phase was separated and extracted with EtOAc. All organic phases were combined, washed with saturated aqueous Na2S2O3 solution, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-40% EtOAc/Hex to give the product 8-benzyl-8-azabicyclo[3.2.1]octan-2-one (39.4 mg, 0.183 mmol) as a syrup. Anal. Calcd. for C14H17NO m/z 215.1, found: 216.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.35-7.21 (5 H, m), 3.68 (2 H, s), 3.36 (2 H, d, J=5.5 Hz), 2.45-2.28 (2 H, m), 2.27-2.16 (3 H, m), 1.81-1.70 (3 H, m).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was then partitioned between EtOAc and water
  3. customThe aqueous phase was separated
  4. extractionextracted with EtOAc
  5. washwashed with saturated aqueous Na2S2O3 solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified
  10. washeluting with a gradient of 0-40% EtOAc/Hex

Sources & evidence

ORD record
ord-6a44a0bd855d468493832560b323885b
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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