Dichloromethane → 8-(2-Chloroethyl)-3-(2-naphthyl)-8-azabicyclo[3.2.1]oct-2-ene

HRID 987576Notes

Reaction equation

HRID 987576 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:17][CH:16]2[N:18]([CH2:19][CH2:20]O)[CH:13]([CH2:14][CH2:15]2)[CH:12]=1.CS([Cl:26])(=O)=O.CCN(CC)CC.C(Cl)Cl>O>[Cl:26][CH2:20][CH2:19][N:18]1[CH:16]2[CH2:15][CH2:14][CH:13]1[CH:12]=[C:11]([C:2]1[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=1)[CH2:17]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 180091722-[3-(2-Naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethanol

Product 1

HCID 180091818-(2-Chloroethyl)-3-(2-naphthyl)-8-azabicyclo[3.2.1]oct-2-eneYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[3-(2-Naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethanol (0.95 g, 3.40 mmol), 0.42 g (3.70 mmol) MsCl, 0.71 mL (515 mg, 5.10 mmol) Et3N and 20 mL CH2Cl2 are stirred at 23 C in for 12 h. The reaction mixture is poured into 200 mL of H2O and extracted with 3×50 mL CH2Cl2. The combined organics are washed with H2O (3×100 mL,) brine (1×100 mL), dried over MgSO4, filtered, and the volatiles are evaporated. Flash chromatography on SiO2 gel, eluting with EtOAc/MeOH (20/1 to 10/1), gives 0.50 g (1.68 mmol, a 50% yield) of the title compound as a tan solid. mp: 122-123° C.; MS (ES) m/z 298 (MH)+.

Workup

  1. extractionextracted with 3×50 mL CH2Cl2
  2. washThe combined organics are washed with H2O (3×100 mL,) brine (1×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe volatiles are evaporated
  6. washFlash chromatography on SiO2 gel, eluting with EtOAc/MeOH (20/1 to 10/1)
  7. customgives 0.50 g (1.68 mmol

Sources & evidence

ORD record
ord-3c02c04b044a409c8986b1f6f8aad795
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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