1-Benzyl-5-thiophen-3-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid ethyl ester → 1-Benzyl-3-thiophen-3-yl-piperidine-4-carboxylic acid ethyl ester

HRID 30269Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH2:7][CH2:8][N:9]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][C:11]=1[C:12]1[CH:16]=[CH:15][S:14][CH:13]=1)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH:11]1[C:12]1[CH:16]=[CH:15][S:14][CH:13]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of the product from step b) (6.69 g, 20.4 mmol) was dissolved in EtOH (37 ml) and treated with 10% Pd/C (Wet Degussa type, 13.4 g) and heated to 40° C. for 2 days under H2 (1 atm). Next, the Pd/C was removed by filtration through celite, replaced with fresh 10% Pd/C (13.4 g) and the reaction was continued for two more days. The Pd/C was removed by filtration through celite and the EtOH was evaporated in vacuo to provide the subtitle compound (4.78 g, 71%). MS calculated for C19H23NO2S+H 330, observed 330.

Workup

customNext, the Pd/C was removed by filtration through celite
customThe Pd/C was removed by filtration through celite
customthe EtOH was evaporated in vacuo

Sources & evidence

ORD record: ord-de03a7b6de03469b824e08f3fe77a04d
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423056B2

Reaction notes

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