Methylamine → rac-(1R*,2R*,4R*)-2-(2-methylamino-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

HRID 220311

Reaction equation

HRID 220311 reaction equation
[OH:1][C@@:2]1([CH2:16][CH2:17]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:7][C@H:6]2[CH2:8][CH2:9][C@@H:3]1[CH:4]=[C:5]2[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:29][NH2:30]>CCO.C(Cl)Cl>[CH3:29][NH:30][CH2:17][CH2:16][C:2]1([OH:1])[CH2:7][CH:6]2[CH2:8][CH2:9][CH:3]1[CH:4]=[C:5]2[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 91466714HCID 91466714, compound

Product 1

HCID 68415512rac-(1R*,2R*,4R*)-2-(2-methylamino-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

4.28 g of rac-toluene-4-sulfonic acid (1R*,2R*,4R*)-2-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl ester (see Example 1, procedures P1.1 and P1.2) were dissolved in a 8 M solution of MeNH2 in EtOH (54 mL). The mixture was stirred overnight at 40° C., diluted with DCM and washed with sat.-NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated to give 2.73 g of rac-(1R*,2R*,4R*)-2-(2-methylamino-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol as a white solid.

Workup

  1. washwashed with sat.-NaHCO3
  2. dry with materialThe organic phase was dried over anh. Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f8334265cda64b44bd81dae7dd072c58
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Linked notes

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