Cyclohexene oxide → HCID 44160187, compound

HRID 517852Notes

Reaction equation

HRID 517852 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[H-].[Na+].[CH:18]12[O:24][CH:23]1[CH2:22][CH2:21][CH2:20][CH2:19]2>CN(C=O)C>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([CH:22]3[CH2:21][CH2:20][CH2:19][CH2:18][CH:23]3[OH:24])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 9246Cyclohexene oxideHCID 24758Sodium hydrideHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-

Product 1

HCID 44160187HCID 44160187, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1 gm, 5 mmol) was taken in DMF (10 ml). NaH (300 mg, 12.5 mmol) was added to it and the reaction mixture stirred at RT for 15 min. 7-oxabicyclo[4.1.0]heptane (0.9 ml, 9.0 mmol) was taken in DMF (3 ml) and added drop wise to the reaction mixture. After complete addition, reaction mixture was heated at 60-65° C. overnight. The reaction was monitored by LCMS. After completion of the reaction, reaction mixture was cooled to RT and quenched with water, extracted with ethyl acetate (3×25 ml), dried over sodium sulfate and concentrated under vacuum to obtain the crude product. This crude was purified by silica gel column chromatography (Eluent: 20% Methanol in DCM) to get 900 mg of 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)cyclohexanol as yellow semi solid. 1H NMR (CDCl3) FREE BASE 7.37-7.30 (m, 2H), 7.20 (s, 1H), 4.37-4.22 (bs, 1H), 3.67-3.64 (s, 1H), 3.61-3.57 (m, 2H), 3.0-2.80 (m, 3H), 2.60-2.40 (m, 7H), 1.98-1.82 (m, 4H), 1.50-1.38 (m, 4H).

Workup

  1. additionadded drop wise to the reaction mixture
  2. additionAfter complete addition, reaction mixture
  3. temperaturewas heated at 60-65° C. overnight
  4. customAfter completion of the reaction, reaction mixture
  5. temperaturewas cooled to RT
  6. customquenched with water
  7. extractionextracted with ethyl acetate (3×25 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customto obtain the crude product
  11. customThis crude was purified by silica gel column chromatography (Eluent: 20% Methanol in DCM)

Sources & evidence

ORD record
ord-c817481447744478b242b7cb763a0009
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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