HCID 178418361, compound → HCID 178472446, compound

HRID 1087650Notes

Reaction equation

HRID 1087650 reaction equation
[C:1]([O:5][C:6](=[O:44])[CH:7]([CH2:28][N:29](CC1C=CC=CC=1)CC1C=CC=CC=1)[CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd].C(OCC)C>[C:1]([O:5][C:6](=[O:44])[CH:7]([CH2:28][NH2:29])[CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:17][CH2:18][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:21]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178472444HCID 178472444, compound

Product 1

HCID 178472446HCID 178472446, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The product from step (c) above (4.6 g, 7.62 mmole) in ethanol (75 ml) was hydrogenated in an atmosphere of hydrogen (50 p.s.i., 3.46 bar) over palladium on charcoal (200 mg), at room temperature overnight. The reaction mixture was filtered through a Solkaflok pad, and the filtrate evaporated to dryness to yield the crude product as an oil. This was dissolved in diethyl ether, and extracted into dilute hydrochloric acid (pH 2) (2x). The combined aqueous layers were washed with diethyl ether, then neutralised with saturated aqueous sodium bicarbonate and extracted with dichloromethane (3x). The combined organic phases were dried (Na2SO4) and evaporated to yield the title amine as an oil (2.91 g, 90%). Found: C,64.80; H,9.28; N,6.76. C23H40N2O5 requires C,65.06; H,9.50; N,6.60%.

Workup

  1. filtrationThe reaction mixture was filtered through a Solkaflok pad
  2. customthe filtrate evaporated to dryness
  3. customto yield the crude product as an oil
  4. extractionextracted into dilute hydrochloric acid (pH 2) (2x)
  5. washThe combined aqueous layers were washed with diethyl ether
  6. extractionextracted with dichloromethane (3x)
  7. dry with materialThe combined organic phases were dried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-c65f2719c31d4b579371d2fe80bfacad
Source dataset
uspto-grants-1991_07
Patent number
US05036104

Reaction notes

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