Water → HCID 67897303, compound

HRID 2248124Notes

Reaction equation

HRID 2248124 reaction equation
[CH3:1][C:2]12[CH:17]([CH3:18])[CH:15]3[NH:16][C:11]4[CH:12]([CH2:14]3)[CH2:13][C:4](=[C:5]([CH:10]=4)[CH:6]=[CH:7][CH2:8][NH:9]1)[CH2:3]2.C(N(C(C)C)CC)(C)C.Br[CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32].O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]12[CH:17]([CH3:18])[CH:15]3[NH:16][C:11]4[CH:12]([CH:14]3[CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])[CH2:13][C:4](=[C:5]([CH:10]=4)[CH:6]=[CH:7][CH2:8][NH:9]1)[CH2:3]2

Participants

7

Reactant 4

HCID 962WaterHCID 700922-Butene, 1-bromo-3-methyl-HCID 81531DiisopropylethylamineHCID 73656241HCID 73656241, compound

Product 1

HCID 67897303HCID 67897303, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1.42 g of 6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-8H-pyrrolo[2,3-i][3]benzazocine and 40 ml of dimethylformamide was added 1.54 ml of diisopropylethyl amine. The mixture was cooled to 0° C. and 0.97 g of 4-bromo-2-methyl-2-butene in 8 ml of dimethylformamide was added, under nitrogen. The mixture was stirred at 0° C. for an additional 1.25 hr, and was poured into water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate and ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate) to afford 0.63 g (35%) of product, mp 62°-65° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate and ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate)

Sources & evidence

ORD record
ord-3f6234889d7b4bdf97b687969ff61306
Source dataset
uspto-grants-1991_08
Patent number
US05037985

Reaction notes

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