Epibromohydrin → HCID 85887676, compound

HRID 490822Notes

Reaction equation

HRID 490822 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[C:13]2[C:8](=[C:9]([OH:14])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[CH2:15](OC1C=CC=C2C=1C=CN2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.BrCC1CO1.[H-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:15]([O:14][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH:7]=[CH:6][N:5]2[CH2:4][CH:2]1[CH2:3][O:1]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 884654-(phenylmethoxy)-1H-indoleHCID 516892Sodium BicarbonateHCID 85887666HCID 85887666, compound

Product 1

HCID 85887676HCID 85887676, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Oxiranylmethyl-4-hydroxy-indole: A mixture of 4-benzyloxyindole (223 mg, 1.0 mmol), 2-bromomethyl-oxirane (168 mg, 1.2 mmol) and 60% sodium hydride (60 mg, 1.5 mmol) in 5 mL THF was refluxed overnight. The solution was poured into NaHCO3 saturated solution (20 mL) and extracted with EtOAc. The organic layer was separated, washed with brine and dried over Na2SO4. The solvent was removed in vacuo. The crude material was purified by column chromatography (1:4, hexane:ethyl acetate) to yield 200 mg of 4-benzyloxy-1-oxiranylmethylindole, which was hydrogenated by 5% Pd/C in 20 mL methanol under H2 (50 psi) to yield 70 mg (37%) of the title compound. 1H NMR (CDCl3): 7.10-7.03 (m, 2H), 6.95 (d, J=8.4 Hz, 1H), 6.56 (dd, J=0.9 Hz, J=3.3 Hz, 1H), 6.51 (dd, J=0.9 Hz, J=7.8 Hz, 1H), 4.40-4.34 (m, 1H), 4.17-4.10 (m, 1H), 3.29-3.26 (m, 1H), 2.81-2.78 (m, 1H), 2.46-2.44 (m, 1H).

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo
  7. customThe crude material was purified by column chromatography (1:4, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-daa8dc29947a445f8563610ccb5c571b
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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