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

HRID 1027553Notes

Reaction equation

HRID 1027553 reaction equation
[CH2:1]([O:5][C:6]1[C:7]([CH:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[N:8][NH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].[CH2:19](O)CCCC.IC1C(C2C3CCN(CC3)C2)=NN(COCC[Si](C)(C)C)C=1.CCO>CCO.C(OCC)(=O)C.C(N(CC)CC)C.CCO.C(N(CC)CC)C>[CH2:1]([O:5][C:6]1[C:7]([CH:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[N:8][NH:9][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:19]

Participants

7

Reactant 4

HCID 702EthanolHCID 62761-PentanolHCID 575480683-[4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-1-azabicyclo[2.2.2]octaneHCID 1784503023-(4-Butoxy-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 2

HCID 22328969EtOH ethyl acetate triethylamineSolventHCID 22663003EtOH 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-368b0f4990d14b3890e48c8efe8318bd
Source dataset
uspto-grants-2014_05
Patent number
US08735388B2

Reaction notes

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