HCID 57846983, compound → HCID 57847254, compound

HRID 735758Notes

Reaction equation

HRID 735758 reaction equation
[C:1]([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[C:16]([N:18]1[C@@H:30]2[C@@H:21]([C@H:22]([C:31]3[N:32](C(OCC4C=CC=CC=4)=O)[CH:33]=[CH:34][CH:35]=3)[NH:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=32)[CH2:20][CH2:19]1)=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[NH:32]1[CH:33]=[CH:34][CH:35]=[C:31]1[C@@H:22]1[C@@H:21]2[CH2:20][CH2:19][N:18]([C:16]([C@H:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]3[NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:17])[C@@H:30]2[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[NH:23]1

Participants

4

Reactant 1

HCID 57846983HCID 57846983, compound

Product 1

HCID 57847254HCID 57847254, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 2-((3aR*,4R*,9bR*)-1-{[(1S,2R)-2-(benzoylamino)cyclohexyl]carbonyl}-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-4-yl)-1H-pyrrole-1-carboxylate (407 mg, 0.67 mmol) was dissolved in methanol (3 ml), 10% palladium on carbon (50% aqueous, 240 mg) was added, and the mixture was stirred under hydrogen atmosphere for 2 hrs. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to column chromatography using silica gel (30 g), and eluted with hexane-ethyl acetate (9:1-4:1, v/v). The title compound (3aR,4R,9bR) (64 mg, 20%) was obtained as a colorless amorphous form from the first eluted fraction.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washeluted with hexane-ethyl acetate (9:1-4:1

Sources & evidence

ORD record
ord-c875456dbebb4f04b63472ebace4797b
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

Loading…