Ethyl 1-cyclohexyl-5-(4-benzyloxyphenyl)-1H-pyrazole-3-carboxylate → [1-cyclohexyl-5-(4-benzyloxyphenyl)-1H-pyrazol-3-yl]methanol

HRID 2216509Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:20][CH:19]=3)=[CH:16][C:15]([C:32](OCC)=[O:33])=[N:14]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C1COCC1>[CH:7]1([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:20][CH:19]=3)=[CH:16][C:15]([CH2:32][OH:33])=[N:14]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of LAH (52 mg, 1.36 mmol) in THF (6 ml) at 0° C., was added dropwise a solution of pyrazole ester 1.3 (500 mg, 1.24 mmol) in THF (3 ml). The mixture was stirred at 0° C. for 30 min, quenched with H2O, diluted with 1N HCl, and extracted with EtOAc (3×). The combined organic phase was washed with H2O, brine, and dried (Na2SO4). Filtration through a 1″ pad of SiO2, elution with ethyl acetate, and concentration of the filtrate afforded 448 mg (100%) alcohol 2.1. HRMS (ESI) calc'd for C23H27N2O2 363.1994; found 363.2083 (MH+).

Workup

customquenched with H2O
additiondiluted with 1N HCl
extractionextracted with EtOAc (3×)
washThe combined organic phase was washed with H2O, brine
dry with materialdried (Na2SO4)
filtrationFiltration through a 1″
washpad of SiO2, elution with ethyl acetate, and concentration of the filtrate

Sources & evidence

ORD record: ord-3c3373b154f440fc8f17cf9702991acb
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112601B2

Reaction notes

Loading…