Ethanol → tert-butyl 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylate

HRID 1918649Notes

Reaction equation

HRID 1918649 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=1.C(O)C>[Pt](=O)=O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 702EthanolHCID 12072032tert-butyl 4-(5-chloro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 12072033tert-butyl 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Platinum(IV) oxide (0.107 g) was added to the suspension of tert-butyl 4-(5-chloro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.05 g; 3.15 mmol) in the mixture of ethanol (20 mL) and acetic acid (10 mL). After degassing, the mixture was subjected to hydrogenation for 20 hours and was filtered through celite. The filtrate was concentrated under reduced pressure to give 1.03 g (98%) of tert-butyl 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylate as a solid.

Workup

  1. customAfter degassing
  2. filtrationwas filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-69fba7a1ad6147558c7c1629dbb6ff25
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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