Benzyl Bromide → HCID 57941448, compound

HRID 1437969Notes

Reaction equation

HRID 1437969 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([N:16]1[C:24](=[O:25])[C:23]2[C@@H:22]3[C:26]([CH3:28])([CH3:27])[C@@:19]([CH3:29])([CH2:20][CH2:21]3)[C:18]=2[NH:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.ClCCl>[CH2:1]([N:17]1[C:18]2[C@@:19]3([CH3:29])[C:26]([CH3:28])([CH3:27])[C@H:22]([CH2:21][CH2:20]3)[C:23]=2[C:24](=[O:25])[N:16]1[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 7498Benzyl BromideHCID 57941397HCID 57941397, compound2×

Product 1

HCID 57941448HCID 57941448, compoundYield 42.7%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of benzyl bromide (300 μL, 2.5 mmol), (4S,7R)-2-benzyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 23; 159 mg, 0.56 mmol), and tetra-n-butylammonium iodide (160 mg, 0.43 mmol) in N,N-dimethylformamide (2 mL) was heated in an oil-bath at 100° C. for 17 h. The reaction mixture was cooled to room temperature and diluted with dichloromethane (125 mL). The solution was washed with water (5×25 mL) and sodium thiosulfate solution (25 mL), dried (magnesium sulfate), filtered, and evaporated and the residue was purified on an Isco 40 g column, eluting with 20-100% ethyl acetate/hexanes to give (4S,7R)-1,2-dibenzyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (89 mg, 42%) as a yellow gum. ES(+)-MS (M+H) 373.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe solution was washed with water (5×25 mL) and sodium thiosulfate solution (25 mL)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue was purified on an Isco 40 g column
  7. washeluting with 20-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6edfded204514a3797b714f4b8b9dbd8
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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