HCID 86307969, compound → HCID 131736294, compound

HRID 1053804Notes

Reaction equation

HRID 1053804 reaction equation
C1([C@@H]([NH:9][C@H:10]2[C@H:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][N:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:11]2)C)C=CC=CC=1>CO.[Pd]>[NH2:9][C@H:10]1[C@H:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][N:12]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:11]1

Participants

4

Reactant 1

HCID 86307969HCID 86307969, compound

Product 1

HCID 131736294HCID 131736294, compoundYield 110.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Trans-1-tert-butyl 4-ethyl 3-(((S)-1-phenylethyl)amino)piperidine-1,4-dicarboxylate 6 (3.7 g, 8.3 mmol, 1.0 equiv) was hydrogenated in the presence of 10% Pd/C (0.37 g) catalyst under H2 at 30 atmospheric pressure in MeOH (100 mL) at 50° C. for 8 h. The catalyst was filtered off and the solvent was removed in vacuo to give (trans)-1-tert-butyl 4-ethyl 3-aminopiperidine-1,4-dicarboxylate 7 as light yellow oil (2.5 g, yield: 92%). ESI-MS (M+H)+: 273.1. 1H NMR (400 MHz, CDCl3) δ: 4.18 (q, 2H), 3.97-3.94 (m, 2H), 3.37 (s, 1H), 3.07-3.02 (m, 1H), 2.89-2.85 (m, 1H), 2.60-2.55 (m, 1H), 2.01-1.91 (m, 1H), 1.70-1.54 (m, 3H), 1.46 (s, 9H), 1.28 (t, 3H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0d027f006907490c9859e1cc71eb0d92
Source dataset
uspto-grants-2016_07
Patent number
US09394277B2

Reaction notes

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