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

HRID 30264Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of the product from step b) (5.83 g, 18 mmol) was dissolved in EtOH (32.4 ml) and treated with 10% Pd/C (Wet Degussa type, 11.7 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 (11.7 g) and the reaction was continued for two more days. The Pd/C was filtered through celite and the EtOH was evaportated in vacuo to provide the subtitle compound (4.5 g, 76%) that was used without further purification. MS calculated for C19H23NO2S+H 330, observed 330.

Workup

customNext, the Pd/C was removed by filtration through celite
filtrationThe Pd/C was filtered through celite

Sources & evidence

ORD record: ord-4f518b63576e4b9995bb5e3cb3d6639b
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423056B2

Reaction notes

Loading…