Diethyl Ether → HCID 86745275, compound

HRID 1197543Notes

Reaction equation

HRID 1197543 reaction equation
[ClH:1].C1(C[NH:9][C@@:10]23[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][C@@H:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)C=CC=CC=1.CCOCC.C(OCC)(=O)C>CO.O1CCCC1.[Pd]>[ClH:1].[CH:23]1[C:18]2[CH2:17][C@H:16]3[C@@:10]([NH2:9])([C:19]=2[CH:20]=[CH:21][CH:22]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 86745276HCID 86745276, compound

Product 1

HCID 86745275HCID 86745275, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the benzylamine from Example 83 in methanol (50 ml) and tetrahydrofuran (50 ml) was added 0.5 g of 20% palladium on carbon. The reaction was hydrogenated for 18 minutes and stopped. The catalyst was removed by filtration and the solvent was concentrated under reduced pressure. The residue was partitioned between 0.1N hydrochloric acid and dichloromethane. The dichloromethane was dried (MgSO4), filtered and concentrated in vacuo to yield a brown oil. The oil was slurried with ether and ethyl acetate and a white solid precipitated to afford the title compound (2.5 g, 54%), mp 224°-226° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customThe residue was partitioned between 0.1N hydrochloric acid and dichloromethane
  4. dry with materialThe dichloromethane was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a brown oil
  8. customa white solid precipitated

Sources & evidence

ORD record
ord-7d1ed17977b54c499a40292e0bb325f3
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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