Benzyl Bromide → HCID 57941320, compound

HRID 1437959Notes

Reaction equation

HRID 1437959 reaction equation
[C:1]1([N:7]2[C:15]3[C@@:14]4([CH3:19])[C:16]([CH3:18])([CH3:17])[C@H:11]([CH2:12][CH2:13]4)[C:10]=3[C:9](=[O:20])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O.O>[CH2:21]([N:8]1[C:9](=[O:20])[C:10]2[C@@H:11]3[C:16]([CH3:17])([CH3:18])[C@@:14]([CH3:19])([CH2:13][CH2:12]3)[C:15]=2[N:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 57250492HCID 57250492, compound2×

Product 1

HCID 57941320HCID 57941320, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (4S,7R)-1-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 8; 1.00 g, 3.7 mmol) and benzyl bromide (0.9 mL, 7.6 mmol) in N,N-dimethylformamide (30 mL) was heated at 100° C. overnight. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and purified using an Analogix Intelliflash 280 system (Analogix, Inc., Burlington, Wis.) with an Isco 80 g column, eluting with 5-75% ethyl acetate/hexanes to give (4S,7R)-2-benzyl-7,8,8-trimethyl-1-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (1.01 g, 76%) as a brown oil. ES(+)-MS (M+H) 359.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified
  7. washeluting with 5-75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1b92b4573734422f813c458464782aae
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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