Potassium Carbonate → Methyl 4-((4-((tert-butoxycarbonyl)amino)piperidin-1-yl)methyl)benzoate

HRID 77508Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1.[C:13]([O:17][C:18](=[O:26])[NH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:23]2[CH2:22][CH2:21][CH:20]([NH:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:26])[CH2:25][CH2:24]2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-bromomethyl-benzoic acid methyl ester (3.0 g; 15 mmol), piperidin-4-yl-carbamic acid tert-butyl ester (3.77 g; 16.5 mmol) and potassium carbonate (4.35 g, 31.5 mmol) in 100 ml acetonitrile is stirred for 5 h at 80° C. Precipitates were removed by filtration and the solution is evaporated. The residue is purified by silica gel column chromatography (gradient: DCM/Methanol 98:2 to 95:5 to yield 4-(4-tert-Butoxycarbonylamino-piperidin-1-ylmethyl)-benzoic acid methyl ester.

Workup

customPrecipitates
customwere removed by filtration
customthe solution is evaporated
customThe residue is purified by silica gel column chromatography (gradient

Sources & evidence

ORD record: ord-b6eafea736c24b79bbb1142f1d8e6b17
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841309B2

Reaction notes

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