(3R,4R)-1-tert-butyl 3-ethyl 4-((R)-1-phenylethylamino)-piperidine-1,3-dicarboxylate → (3R,4R)-1-tert-butyl 3-ethyl 4-aminopiperidine-1,3-dicarboxylate

HRID 497444Notes

Reaction equation

HRID 497444 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([NH:12][C@@H](C2C=CC=CC=2)C)[CH2:10][CH2:9][N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:7]1)=[O:5])[CH3:2]>[OH-].[Pd+2].[OH-].C(O)C>[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([NH2:12])[CH2:10][CH2:9][N:8]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 11080151(3R,4R)-1-tert-butyl 3-ethyl 4-((R)-1-phenylethylamino)-piperidine-1,3-dicarboxylate

Product 1

HCID 58745614(3R,4R)-1-tert-butyl 3-ethyl 4-aminopiperidine-1,3-dicarboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

In a dry 500-mL Paar flask charged with Palladium hydroxide (20 wt % Pd, dry basis, on carbon, 1.50 g) was added ethanol (75 mL) and (3R,4R)-4-[(R)-1-phenyl-ethylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (4.30 g, 11.4 mmol). The reaction mixture was hydrogenated at 53 psi for 20.5 hours with vigorous shaking. The reaction mixture was filtered through a plug of celite. The plug was washed with 20 mL of ethanol and the combined filtrates were concentrated in vacuo to give a colorless oil (3.07 g, 99%). 1H NMR (300 MHz, CDCl3), δ: 4.32 (bs, 1H), 4.19 (q, 2H, J=7), 4.19 (bs, 1H), 3.08 (td, 1H, J=11, J′=3), 2.75 (bt, 2H, J=14), 2.29 (td, 1H, J=11, J′=4), 1.89 (m, 1H), 1.46 (s, 9H), 1.38 (td, 1H, J=12, J′=5), 1.28 (t, 3H, J=7).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washThe plug was washed with 20 mL of ethanol
  3. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-f980eb79b4874e1b9dc7b077720ebdbc
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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