Ethanol → 3-(4-Pentyloxy-1H-pyrazol-3-yl)-1-azabicyclo[2.2.2]octane

HRID 2043055Notes

Reaction equation

HRID 2043055 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5].I[C:8]1[C:9]([CH:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[N:10][N:11](COCC[Si](C)(C)C)[CH:12]=1.CCO.CCO.C(N(CC)CC)C>CCO.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([O:6][C:8]1[C:9]([CH:21]2[CH:26]3[CH2:25][CH2:24][N:23]([CH2:28][CH2:27]3)[CH2:22]2)=[N:10][NH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 62761-PentanolHCID 22663003EtOH triethylamineHCID 575480683-[4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-1-azabicyclo[2.2.2]octane

Product 1

HCID 1784469773-(4-Pentyloxy-1H-pyrazol-3-yl)-1-azabicyclo[2.2.2]octane

Reagents, catalysts & solvents 1

HCID 22328969EtOH ethyl acetate triethylamineSolvent

Procedure

Compound 52C was prepared following the procedure as described for the synthesis of compound 52A (see Scheme 10) using pentanol (25 ml) and 3-[4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-1-azabicyclo[2.2.2]octane (50), (2 g, 4.61 mmol). Work-up and flash chromatography (gradient EtOH to EtOH/triethylamine 300/1) followed by a second flash chromatography (EtOH/ethyl acetate/triethylamine 25/75/1) afforded compound 51C as an oil (0.46 g, 15%). LCMS (method B); Rt: 3.30 min, ([M+H]+=394).

Sources & evidence

ORD record
ord-0249ab5bf0fc4923a8b42fd2bbf4ad5e
Source dataset
uspto-grants-2013_11
Patent number
US08586606B2

Reaction notes

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