Sodium hydride → (S)-(+)-4-(2,3-Epoxypropoxy)carbazole

HRID 40631

Reaction equation

HRID 40631 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[C:4]([OH:14])=[CH:3][CH:2]=1.[H-].[Na+].[N+](C1C=C(S(O[CH2:30][C@H:31]2[O:33][CH2:32]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C>[O:33]1[CH2:32][C@H:31]1[CH2:30][O:14][C:4]1[C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1042514-HydroxycarbazoleHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9H-Carbazol-4-ol (0.367 g, 2.0 mmol) was placed in a flask with DMF (10 mL) and NaH (60% dispersion in oil, 77 mg, 2.0 mmol) and stirred for 30 min at room temperature. (S)-glycidyl 3-nitrobenzene sulfonate (0.52 g, 2.0 mmol) was added to the reaction mixture, which was then stirred at room temperature for 14 hours. The reaction was quenched with NaHCO3 (saturated) and then extracted with ethyl acetate (3×). The organic layer was dried with magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield crude product which was purified by silica gel chromatography (60% Ethyl acetate/heptane) to yield the title compound as a residue.

Workup

  1. stirringwas then stirred at room temperature for 14 hours
  2. customThe reaction was quenched with NaHCO3 (saturated)
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customto yield crude product which
  8. customwas purified by silica gel chromatography (60% Ethyl acetate/heptane)

Sources & evidence

ORD record
ord-e8c5a1c36f5d4ec695ceb777a2da6bf8
Source dataset
uspto-grants-2013_09
Patent number
US08530475B2

Linked notes

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