benzyl 8-(1-(tert-butoxycarbonyl)piperidin-4-ylcarbamoyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate → HCID 66589660, compound

HRID 340399Notes

Reaction equation

HRID 340399 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[CH:25]=[CH:24][C:23]3[NH:22][C:21]4[CH2:26][CH2:27][N:28](C(OCC5C=CC=CC=5)=O)[CH2:29][C:20]=4[C:19]=3[CH:18]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[CH2:29]1[C:20]2[C:19]3[CH:18]=[C:17]([C:15]([NH:14][CH:11]4[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]4)=[O:16])[CH:25]=[CH:24][C:23]=3[NH:22][C:21]=2[CH2:26][CH2:27][NH:28]1

Participants

4

Reactant 1

HCID 44177302benzyl 8-(1-(tert-butoxycarbonyl)piperidin-4-ylcarbamoyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 66589660HCID 66589660, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl 8-(1-(tert-butoxycarbonyl)piperidin-4-ylcarbamoyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (8, 20.98 g, 39 mmol) and Pd/C (10% wt.) (4.0 g) in MeOH (300 mL) was allowed to stir at room temperature overnight. The palladium was then filtered, washed with MeOH and the resulting clear solution was concentrated to give tert-butyl 4-(2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamido)piperidine-1-carboxylate as a white foamy residue (11.63 g, 74%) ppm; MS (ES) 399 (M+H).

Workup

  1. filtrationThe palladium was then filtered
  2. washwashed with MeOH
  3. concentrationthe resulting clear solution was concentrated

Sources & evidence

ORD record
ord-d7cda0f606de459388143fcf3ee25444
Source dataset
uspto-grants-2014_11
Patent number
US08895578B2

Reaction notes

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