HCID 69283221, compound → HCID 69282983, compound

HRID 901092Notes

Reaction equation

HRID 901092 reaction equation
C([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18]([C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])=[CH:17]3)[CH2:9]1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C.CO>[N:25]1([C:23]([C:18]2[NH:19][C:20]3[C:16]([CH:17]=2)=[CH:15][C:14]([O:13][C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:22][CH:21]=3)=[O:24])[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1

Participants

4

Reactant 1

HCID 69283221HCID 69283221, compound

Product 1

HCID 69282983HCID 69282983, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 4.6 (0.016 mol) [5-((S)-1-Benzyl-pyrrolidin-3-yloxy)-1H-indol-2-yl]-morpholin-4-yl-methanone and 480 mg of 10% palladium on charcoal in 250 ml ethyl actetate/acetic acid 9/1 was hydrogenated at room temperature during 4 h. After filtration the filtrate was evaporated to dryness and the residue was taken up in 250 ml DCM and 150 ml 10% Na2CO3. The aqueous phase was extracted with 2×100 ml DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness to yield 2.77 g (77% of the title compound as off white solid. MS (m/e): 316.1 (MH+, 100%).

Workup

  1. filtrationAfter filtration the filtrate
  2. customwas evaporated to dryness
  3. extractionThe aqueous phase was extracted with 2×100 ml DCM
  4. dry with materialthe combined organic phases were dried with Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-38a613c6d0b642d585f19193f375a69b
Source dataset
uspto-grants-2008_04
Patent number
US07361682B2

Reaction notes

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