HCID 86672430, compound → HCID 86672429, compound

HRID 41208Notes

Reaction equation

HRID 41208 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([C:15]3[N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:17]=[CH:18][CH:19]=3)[CH:14]=1)[O:11][C:10]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[CH:9][C:8]2=[O:33])=[O:4]>CO.[Rh].[Pd]>[CH3:34][N:2]([CH3:1])[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([CH:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=1)[O:11][C:10]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[CH:9][C:8]2=[O:33])=[O:4]

Participants

5

Reactant 1

HCID 86672430HCID 86672430, compound

Product 1

HCID 86672429HCID 86672429, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 2-(6-(dimethylcarbamoyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate (0.6 g, 1.28 mmol) in MeOH (10 mL) was hydrogenated over 5% Rh/Al2O3 (NanoThales CatCart cartridge, product ID THS 02118) with the H-Cube (Continuous flow hydrogenation apparatus HC-2.5S from THALES Nanotechnology Inc. Budapest H-1031; Zahony u.7.; Hungaria) at 10 bars, 50° C. and a flow rate of 1 mL/min. for 3.5 h with continuous recycling. The cartridge was replaced by a 10% Pd/c cartridge and hydrogenation was pursued for 6 h at 60 bars and 60° C. The mixture was evaporated to dryness to give a solid which was triturated in diethyl ether, filtered and dried under vacuum at 50° C. to afford pure tert-butyl 2-(6-(dimethylcarbamoyl)-2-morpholino-4-oxo-4H-chromen-8-yl)pyrrolidine-1-carboxylate (0.30 g, 50%) as a white solid. The crude product was used as such for the next step. Mass Spectrum: m/z [M+H]+=472.

Workup

  1. waitwas pursued for 6 h at 60 bars and 60° C
  2. customThe mixture was evaporated to dryness
  3. customto give a solid which
  4. customwas triturated in diethyl ether
  5. filtrationfiltered
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-036c2f16253e409392004d8e2fe6cc80
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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