HCID 86688814, compound → HCID 86688813, compound

HRID 1412933Notes

Reaction equation

HRID 1412933 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:34]3[C:10](=[C:11]4[C:31](=[CH:32][CH:33]=3)[C:15]3[N:16]=[C:17]([C@@H:19]5[CH2:23][CH2:22][CH2:21][N:20]5[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[NH:18][C:14]=3[CH2:13][CH2:12]4)[O:9][CH2:8][C:6]=2[CH:7]=1>ClCCl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:34]3[C:10](=[C:11]4[C:31](=[CH:32][CH:33]=3)[C:15]3[N:16]=[C:17]([C@@H:19]5[CH2:23][CH2:22][CH2:21][N:20]5[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[NH:18][C:14]=3[CH:13]=[CH:12]4)[O:9][CH2:8][C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 86688814HCID 86688814, compound

Product 1

HCID 86688813HCID 86688813, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate tert-butyl(2S)-2-(9-chloro-3,4,5,7-tetrahydroisochromeno[3′,4′:5,6]naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (1.43 g, 3.0 mmol) in dichloromethane (30 mL) was added manganese(IV) oxide (15 g, 198 mmol). The mixture was stirred for four hours at room temperature then filtered through Celite. The MnO2 was thoroughly rinsed with dichloromethane and the total filtrate was concentrated to yield tert-butyl(2S)-2-(9-chloro-3,7-dihydroisochromeno[3′,4′:5,6]naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (1.37 g, 96% yield). This material was used without further purification.

Workup

  1. filtrationthen filtered through Celite
  2. washThe MnO2 was thoroughly rinsed with dichloromethane
  3. concentrationthe total filtrate was concentrated

Sources & evidence

ORD record
ord-8cd52d0c1c1d4a329155c3d499ea7247
Source dataset
uspto-grants-2014_12
Patent number
US08921341B2

Reaction notes

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