Red-Al → HCID 66877393, compound

HRID 453713Notes

Reaction equation

HRID 453713 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[N:10]=[C:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:34])[C:16](=O)[CH2:17][C:18]3([OH:32])[CH2:23][CH:22]4[CH2:24][CH2:25][CH:19]3[CH:20]=[C:21]4[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:8][C:7]=2[C:6]([O:35][CH3:36])=[CH:5][CH:4]=1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH3:36][O:35][C:6]1[C:7]2[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:34])[CH2:16][CH2:17][C:18]3([OH:32])[CH2:23][CH:22]4[CH2:24][CH2:25][CH:19]3[CH:20]=[C:21]4[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:10][C:11]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 77305456HCID 77305456, compound

Product 1

HCID 66877393HCID 66877393, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 310 mg of rac-(1R*,2R*,4R*)-N-[3-(4,7-dimethoxy-1H-benzoimidazol-2-yl)-propyl]-2-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-N-methyl-acetamide in 8 mL toluene were added dropwise 0.77 mL of a Red-Al solution (65% in toluene) at 0° C. After stirring for 10 min at 0° C., the cooling bath was removed and stirring was continued for 3 h at rt. The reaction mixture was then carefully poured onto a mixture of 1M NaOH/ice and stirred for 10 min. The aq. phase was extracted with toluene, the combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by CC using EtOAc-MeOH (2:1) yielded 230 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(4,7-dimethoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol as white foam.

Workup

  1. customthe cooling bath was removed
  2. stirringstirring
  3. waitwas continued for 3 h at rt
  4. additionThe reaction mixture was then carefully poured onto a mixture of 1M NaOH/ice
  5. stirringstirred for 10 min
  6. extractionThe aq. phase was extracted with toluene
  7. washthe combined organic phases were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customPurification by CC

Sources & evidence

ORD record
ord-fadf4de03ef04b21b87964155a14ce63
Source dataset
uspto-grants-2013_07
Patent number
US08492555B2

Reaction notes

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