Carbazole → HCID 736403, compound

HRID 1776166Notes

Reaction equation

HRID 1776166 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl[CH2:17][C@H:18]1[CH2:20][O:19]1>CN(C)C=O>[O:19]1[CH2:20][C@@H:18]1[CH2:17][N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 14797Potassium HydroxideHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 736403HCID 736403, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of carbazole (2.0 g, 12 mmol) in anhydrous N,N-dimethylformamide (20 mL) was added 85% aqueous potassium hydroxide (0.95 g, 14.4 mmol) and the mixture was stirred at room temperature for 1 hour. The mixture was cooled in an ice bath and (R)-(−)-2-(chloromethyl)oxirane (2.77 g, 29.9 mmol) was added. The mixture was stirred overnight at room temperature, and then partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated. The residue was purified by recrystallization from ethyl acetate/hexanes to afford the desired product as white crystals (0.8 g, 30%). 1H NMR (300 MHz, CDCl3) δ 8.10 (d, 2H, J=7.5 Hz), 7.55-7.40 (m, 4H), 7.32-7.22 (m, 2H), 4.66 (dd, 1H, J=15.9, 3.3 Hz), 4.43 (dd, 1H, J=15.9, 4.8 Hz), 3.38 (m, 1H), 2.83 (t, 1H, J=4.5 Hz), 2.60 (dd, 1H, J=4.8, 2.4 Hz).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. stirringThe mixture was stirred overnight at room temperature
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-65a215e0d5af414fb4b0cbf35269254c
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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