HCID 77230727, compound → 1H-Pyrrolo[3,2-b]pyridine-1-carboxylic acid, octahydro-7-methyl-, 1,1-dimethylethyl ester

HRID 1428257Notes

Reaction equation

HRID 1428257 reaction equation
Cl[C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]2=[C:4]([CH3:18])[CH:3]=1>[Pt](=O)=O>[CH3:18][CH:4]1[CH2:3][CH2:2][NH:7][CH:6]2[CH2:8][CH2:9][N:10]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH:5]12

Participants

3

Reactant 1

HCID 77230727HCID 77230727, compound

Product 1

HCID 680519971H-Pyrrolo[3,2-b]pyridine-1-carboxylic acid, octahydro-7-methyl-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

To the product of Step 1 (361 mg, 1.35 mmol) was added platinum(IV) oxide (310 mg, 1.37 mmol) in a Parr pressure flask. The flask was purged with nitrogen by successive evacuation/nitrogen backfills and then acetic acid (15 mL) was added. The reaction mixture was placed under hydrogen atmosphere by successive evacuation/hydrogen backfills and the reaction was shaken at 40 psi for 5 days. The reaction was then filtered through Celite and washed with AcOH and concentrated in vacuo to afford a crude oil that was taken onto the next step without further purification. LRMS calc'd for C13H25N2O2 [M+H]+, 241; found 241.

Workup

  1. customThe flask was purged with nitrogen by successive evacuation/nitrogen backfills
  2. additionacetic acid (15 mL) was added
  3. filtrationThe reaction was then filtered through Celite
  4. washwashed with AcOH
  5. concentrationconcentrated in vacuo
  6. customto afford a crude oil that
  7. customwas taken onto the next step without further purification

Sources & evidence

ORD record
ord-b6f723df281d4919b2589624559ff297
Source dataset
uspto-grants-2015_01
Patent number
US08937077B2

Reaction notes

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