Sodium Carbonate → HCID 58503489, compound

HRID 72835Notes

Reaction equation

HRID 72835 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Cl-].[Li+].C([O-])([O-])=O.[Na+].[Na+].[CH2:20]([N:27]1[CH:32]2[CH2:33][CH2:34][CH:28]1[CH:29]=[C:30](OS(C(F)(F)F)(=O)=O)[CH2:31]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC.O>[CH2:20]([N:27]1[CH:32]2[CH2:33][CH2:34][CH:28]1[CH:29]=[C:30]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:31]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 433294Lithium ChlorideHCID 498359108-Benzyl-3-(trifluoromethylsulfonyloxy)-8-azabicyclo[3.2.1]oct-3-ene

Product 1

HCID 58503489HCID 58503489, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Methoxyphenyl boronic acid (0.50 g), lithium chloride (0.26 g), Pd(PPh3)4 (0.17 g), and finally 2 M aqueous Na2CO3 solution (3.2 mL) are added in turn to a flask charged with a stir bar, trifluoromethanesulfonic acid 8-benzyl-8-aza-bicyclo[3.2.1]oct-2-en-3-yl ester (1.0 g), water (5 mL), and 1,2-dimethoxyethane (25 mL) under argon atmosphere. The resulting mixture is stirred at reflux temperature for 5 h. After cooling to ambient temperature, brine is added and the mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and the solvent is removed under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→1:1).

Workup

  1. additioncharged with a stir bar
  2. temperatureat reflux temperature for 5 h
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe combined extracts are dried (Na2SO4)
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→1:1)

Sources & evidence

ORD record
ord-69cee5192e414aff8ce54bb55ce00555
Source dataset
uspto-grants-2014_09
Patent number
US08829027B2

Reaction notes

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