HCID 21959486, compound → HCID 68829191, compound

HRID 887570Notes

Reaction equation

HRID 887570 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:28])([CH3:27])[CH2:9][N:10]2[CH2:13][CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:6][CH:5]=1)([O-])=O>CO>[CH3:27][C:8]1([CH3:28])[C:7]2[C:11](=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=2)[N:10]([CH2:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:9]1

Participants

3

Reactant 1

HCID 21959486HCID 21959486, compound

Product 1

HCID 68829191HCID 68829191, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-[(6-nitro-3,3-dimethylindolinyl)-methyl]piperidinecarboxylate (900 mg) was dissolved in 10 mL MeOH, the mixture was bubbled with H2 for 10 min. 10% Pd/C (30 mg) was added and the mixture was stirred under H2 overnight. The mixture was filtered through Celite® and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 1:1 Hexane:EtOAc to afford a colorless oil. MS: 360 (M+1). Calc'd. for C21H33N3O2—359.5.

Workup

  1. customthe mixture was bubbled with H2 for 10 min
  2. addition10% Pd/C (30 mg) was added
  3. filtrationThe mixture was filtered through Celite®
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography on silica gel with 1:1 Hexane
  6. customEtOAc to afford a colorless oil

Sources & evidence

ORD record
ord-bb86e8a570da4861b71d5f25bc259131
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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