Dabco → 4-(tert-Butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl Ester

HRID 1179937Notes

Reaction equation

HRID 1179937 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[I-].[C:18]([Si:22]([CH3:39])([CH3:38])[O:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30](N2C=C[N+](C)=C2)=[O:31])[CH2:26][CH2:25]1)([CH3:21])([CH3:20])[CH3:19].N12CCN(CC1)CC2>CN(C)C=O>[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:30]([N:27]2[CH2:28][CH2:29][CH:24]([O:23][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:38])[CH3:39])[CH2:25][CH2:26]2)=[O:31])=[N:7][CH:6]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 86589184HCID 86589184, compoundHCID 178522251HCID 178522251, compound

Product 1

HCID 695176994-(tert-Butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl EsterYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of N-(6-hydroxy-pyridin-3-yl)-benzamide (214 mg, 1.00 mmol), 3-[4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carbonyl]-1-methyl-3H-imidazol-1-ium iodide (451 mg, 1.00 mmol) and 1,4-diazabicyclo[2,2,2]octane (112 mg, 1.00 mmol) in dimethylformamide (10 mL) was stirred for 18 hours at room temperature followed by heating for 3 days at 40° C. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 40:60), yielding the title compound (364 mg, 77% yield)

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 40:60)

Sources & evidence

ORD record
ord-8a677a2c762f4c9f9ca4e068c04f575f
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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