Methanol → HCID 131720615, compound

HRID 1599376Notes

Reaction equation

HRID 1599376 reaction equation
[CH2:1]=[CH:2][CH:3]1[CH:8]2[CH2:9][CH:10]([C@H:11]([OH:23])[C:12]3[CH:21]=[CH:20][N:19]=[C:18]4[C:13]=3[CH:14]=[C:15]([OH:22])[CH:16]=[CH:17]4)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH2:30]([O:32][C:33](=[O:38])[CH2:34][CH2:35][CH2:36]Br)[CH3:31].CO>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1.O>[OH-:22].[NH4+:5].[CH2:30]([O:32][C:33](=[O:38])[CH:34]([O:22][C:15]1[CH:14]=[C:13]2[C:18]([N:19]=[CH:20][CH:21]=[C:12]2[CH:11]([OH:23])[C@@H:10]2[N:5]3[CH2:6][CH2:7][C@H:8]([C@@H:3]([CH:2]=[CH2:1])[CH2:4]3)[CH2:9]2)=[CH:17][CH:16]=1)[CH2:35][CH3:36])[CH3:31]

Participants

9

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 51196O-DesmethylquinidineHCID 76300Ethyl 4-bromobutyrate

Product 2

HCID 14923Ammonium HydroxideHCID 131720615HCID 131720615, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 250 mg (0.80 mmol) of (1) in 6 ml of dry dimethylformamide (Aldrich, 99%) was added 110 mg (0.80 mmol) of anhydrous potassium carbonate, followed by 109 ml (0.75 mmol) of ethyl-4-bromobutyrate and catalytic amount (4 mg) of 18-crown 6. The reaction mixture was heated at 120° C. for 2 h, cooled, and placed under reduced pressure to remove dimethylformamide. 50 ml of dichloromethane was added to the residue and the mixture was filtered. The filtrate was washed with 2×25 ml of 5% sodium hydroxide, brine, dried (anhydrous sodium sulphate) and concentrated. The residue was purified on preparative thin layer chromatography using a mixture of 6:1:1:1 ethyl acetate:methanol:water:concentrated ammonium hydroxide as the eluent and yielded 160 mg (0.37 mmol, 45%) of (5) as brown oil. MS, IR and NMR data confirmed the identity of the compound.

Workup

  1. temperaturecooled
  2. customto remove dimethylformamide
  3. addition50 ml of dichloromethane was added to the residue
  4. filtrationthe mixture was filtered
  5. washThe filtrate was washed with 2×25 ml of 5% sodium hydroxide, brine
  6. dry with materialdried (anhydrous sodium sulphate)
  7. concentrationconcentrated
  8. customThe residue was purified on preparative thin layer chromatography
  9. additiona mixture of 6:1:1:1 ethyl acetate

Sources & evidence

ORD record
ord-b44daaab36f444b5bc500dda18228a83
Source dataset
uspto-grants-1998_04
Patent number
US05741715

Reaction notes

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