Cesium carbonate → 1-tert-Butyl 2-methyl (2S,4R)-4-[(3-allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 2045723Notes

Reaction equation

HRID 2045723 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].BrC1C=CC(S([O:17][C@@H:18]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)(=O)=O)=CC=1.[CH2:34]([CH:37]1[CH:46](O)[C:45]23[N:48]=[CH:49][CH:50]=[C:44]2[CH:43]=[CH:42][CH:41]=[C:40]3[N:39]([CH3:51])[CH2:38]1)[CH:35]=[CH2:36]>CN1C(=O)CCC1.CCOC(C)=O.Cl>[CH2:34]([CH:37]1[CH:46]([O:17][C@H:18]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)[C:45]23[N:48]=[CH:49][CH:50]=[C:44]2[CH:43]=[CH:42][CH:41]=[C:40]3[N:39]([CH3:51])[CH2:38]1)[CH:35]=[CH2:36]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 668963203-Allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-ol

Product 1

HCID 866495141-tert-Butyl 2-methyl (2S,4R)-4-[(3-allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylateYield 44%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

Cs2CO3 (8.20 g, 25.20 mmol) and 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (3.80 g, 8.18 mmol) were added in sequence to a solution of 3-allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-ol (1.50 g, 6.29 mmol) in NMP (42 mL). The mixture was heated at 60° C. for 12 h, then cooled and diluted with EtOAc and aqueous HCl (1 N). The organic layer was separated, washed with brine and dried over Na2SO4. Filtration and removal of the volatiles gave a residue that was purified on silica gel (gradient elution, 20-100% EtOAc/petrol ether) to afford the title compound (1.30 g, 44%) as a solid. LCMS (ES+) m/z 466 (M+H)+.

Workup

  1. temperaturecooled
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and removal of the volatiles
  6. customgave a residue that
  7. customwas purified on silica gel (gradient elution, 20-100% EtOAc/petrol ether)

Sources & evidence

ORD record
ord-978cf036560348e8863acaf23c490a67
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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