HCID 118075703, compound → HCID 118076055, compound

HRID 1051732Notes

Reaction equation

HRID 1051732 reaction equation
[H][H].[C:3]([N:6]1[C:15]2[C:10](=[C:11]([O:29][CH2:30][CH2:31][CH3:32])[C:12]([C:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]=3)=[CH:13][CH:14]=2)[CH2:9][CH2:8][C@@H:7]1[CH3:33])(=[O:5])[CH3:4]>CO.[OH-].[OH-].[Pd+2]>[C:3]([N:6]1[C:15]2[C:10](=[C:11]([O:29][CH2:30][CH2:31][CH3:32])[C:12]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:18][CH2:17]3)=[CH:13][CH:14]=2)[CH2:9][CH2:8][C@@H:7]1[CH3:33])(=[O:5])[CH3:4]

Participants

5

Reactant 2

HCID 118075703HCID 118075703, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118076055HCID 118076055, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Balloon pressured hydrogen gas was charged into a round bottom flask containing a suspension of (S)-tert-butyl 4-(1-acetyl-2-methyl-5-propoxy-1,2,3,4-tetrahydroquinolin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (500 mg, 1.17 mmol) and 20% palladium hydroxide on carbon (30 mg, 0.21 mmol) in methanol (10 mL). The reaction was stirred under balloon pressure for 2 hours. The reaction was vented to nitrogen and filtered through a pad of Celite. The filtered solution was concentrated in vacuo and purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 20-40% ethyl acetate-hexane) to afford tert-butyl (S)-4-(1-acetyl-2-methyl-5-propoxy-1,2,3,4-tetrahydroquinolin-6-yl)piperidine-1-carboxylate (500 mg, 100%) as a colorless oil. MS (ESI, pos. ion) m/z 432 [M+H]+.

Workup

  1. additionwas charged into a round bottom flask
  2. additioncontaining
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe filtered solution was concentrated in vacuo
  5. custompurified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 20-40% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-abf8b5a81c744aacbceb36e096856dd3
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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