HCID 86604970, compound → methyl 2-[2-(aminomethyl)phenyl]-3-cyclohexyl-1-(1,3-dioxolan-2-ylmethyl)-1H-indole-6-carboxylate

HRID 1714057Notes

Reaction equation

HRID 1714057 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH:21]3[O:25][CH2:24][CH2:23][O:22]3)[C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH:32]=[N:33]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CC(O)=O.[Pt](=O)=O>[NH2:33][CH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:8]1[N:9]([CH2:20][CH:21]2[O:25][CH2:24][CH2:23][O:22]2)[C:10]2[C:15]([C:7]=1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2

Participants

4

Reactant 1

HCID 86604970HCID 86604970, compound

Product 1

HCID 68508525methyl 2-[2-(aminomethyl)phenyl]-3-cyclohexyl-1-(1,3-dioxolan-2-ylmethyl)-1H-indole-6-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent2×

Procedure

Platinum (IV) oxide (20 mol %) was added as a slurry in AcOH under N2 to a solution of methyl 3-cyclohexyl-1-(1,3-dioxolan-2-ylmethyl)-2-{2-[(hydroxyimino)methyl]phenyl}-1H-indole-6-carboxylate in AcOH (0.07 M). The atmosphere in the reaction vessel was charged with H2 at 50 psi pressure and the reaction agitated on a Parr apparatus for 48 h. The reaction was then filtered under N2 through a plug of celite, washing well with AcOH, and the filtered solution concentrated in vacuo to afford the title compound (100%); MS (ES+) m/z 449 (M+H)+.

Workup

  1. additionThe atmosphere in the reaction vessel was charged with H2 at 50 psi pressure
  2. filtrationThe reaction was then filtered under N2 through a plug of celite
  3. washwashing well with AcOH
  4. concentrationthe filtered solution concentrated in vacuo

Sources & evidence

ORD record
ord-af62bf2b717e4f9bbc598c4e8963b507
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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