Diethyl Pyrocarbonate → HCID 57847162, compound

HRID 735764Notes

Reaction equation

HRID 735764 reaction equation
[CH3:1][C@:2]12[CH2:14][CH2:13][NH:12][C@H:11]1[C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:4][C@H:3]2[C:15]1[CH:19]=[CH:18][S:17][CH:16]=1.[C:20]([NH:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@@H:30]1[C:35](O)=[O:36])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.CCOC(OC(OCC)=O)=O.C(=O)([O-])O.[Na+]>O1CCCC1.C(#N)C>[CH3:1][C@@:2]12[CH2:14][CH2:13][N:12]([C:35]([C@H:30]3[CH2:31][CH2:32][CH2:33][CH2:34][C@H:29]3[NH:28][C:20](=[O:27])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:36])[C@@H:11]1[C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:4][C@@H:3]2[C:15]1[CH:19]=[CH:18][S:17][CH:16]=1

Participants

8

Reactant 5

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 1268229(+)-cis-2-Benzamidocyclohexanecarboxylic AcidHCID 57846949HCID 57846949, compound

Product 1

HCID 57847162HCID 57847162, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (3aS,4R*,9bR*)-3a-methyl-4-(3-thienyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline (750 mg, 2.77 mmol), (1S,2R)-2-(benzoylamino)cyclohexanecarboxylic acid (685 mg, 2.77 mmol), triethylamine (606 mg, 6.10 mmol), acetonitrile (14 ml) and tetrahydrofuran (14 ml) was added DEPC (500 mg, 3.05 mmol) under ice-cooling, and the mixture was stirred for 10 min. The mixture was allowed to return to room temperature and stirred for 12 hrs. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was dried (over anhydrous Na2SO4), and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using silica gel (100 g), and eluted with hexane-ethyl acetate (4:1-1:1, v/v) to give the title compound (3aR,4R,9bR) (110 mg, 8%) as an amorphous form from the first eluted fraction.

Workup

  1. temperaturecooling
  2. customto return to room temperature
  3. stirringstirred for 12 hrs
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried (over anhydrous Na2SO4)
  6. customthe solvent was evaporated under reduced pressure
  7. washeluted with hexane-ethyl acetate (4:1-1:1

Sources & evidence

ORD record
ord-a184d02f53ed42118a5a9e8863636591
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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