Ethanol → 4-[5-(4-Methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 533112Notes

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 4-[5-(4-methanesulfonyl-phenyl)-benzofuran-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.70 g), 10% palladium on carbon (200 mg), ethanol (100 mL), and ethyl acetate (50 mL) is shaken under hydrogen atmosphere (5 bar) at 45° C. until the starting material is completely consumed. The catalyst is filtered off, the filtrate is concentrated in vacuo, and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate/methanol 70:30:0→50:40:10) to give the title compound. LC (method 1): tR=1.75 min; Mass spectrum (ESI+): m/z=458 [M+H]+.

Workup

customis completely consumed
filtrationThe catalyst is filtered off
concentrationthe filtrate is concentrated in vacuo
customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate/methanol 70:30:0→50:40:10)

Sources & evidence

ORD record: ord-21d9dee47c2d4410ad555d81316ee424
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853239B2

Reaction notes

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