Acetic Acid → 4-[5-(4-Methanesulfonylphenyl)-2,3-dihydrofuro[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1622228Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:32][C:17]3=[CH:18][N:19]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=4)[CH:21]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]2[O:32][C:17]3=[CH:18][N:19]=[C:20]([C:22]4[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:26][CH:27]=4)[CH:21]=[C:16]3[CH2:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-[5-(4-methanesulfonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (155 mg), acetic acid (4.0 mL) and 10% palladium on carbon (40 mg) in methanol (10 mL) is shaken under an hydrogen atmosphere (5 bar) at 50° C. The catalyst is filtered off and the filtrate is concentrated in vacuo to give the title compound. LC (method 5): tR=1.32 min; Mass spectrum (ESI+): m/z=459 [M+H]+.

Workup

filtrationThe catalyst is filtered off
concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record: ord-fe262e417a6043a0bd8d1c150ec7435d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778926B2

Reaction notes

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