Cyclopentylhydrazine hydrochloride → (2-(1-cyclopentyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol

HRID 1484770Notes

Reaction equation

[Si]([O:8][CH2:9][C:10]1[C:11]([C:16](=O)/[CH:17]=[CH:18]/[N:19](C)C)=[N:12][CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.Cl.[CH:24]1([NH:29]N)[CH2:28][CH2:27][CH2:26][CH2:25]1>CCO>[CH:24]1([N:29]2[C:16]([C:11]3[C:10]([CH2:9][OH:8])=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:17][CH:18]=[N:19]2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

Conditions

Temperature: 80 °C

Procedure

To (E)-1-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-3-(dimethylamino)prop-2-en-1-one (crude, 3.205 g, 10.0 mmol, 1 eq.) in EtOH (30 mL) was added cyclopentylhydrazine HCl salt (1.639 g, 12.0 mmol, 1.2 eq) at RT. The mixture was heated at 80° C. for 2 h, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give a mixture of regio-isomers, the less polar (2-(1-cyclopentyl-1H-pyrazol-5-yl)pyridin-3-yl)methanol was obtained as a light brown oil (440 mg). MS (ESI) m/z 244.2 [M+H]+.

Workup

concentrationconcentrated
custompurified on silica gel using
additiona mixture of EtOAc and hexanes as eluent
customto give
additiona mixture of regio-isomers

Sources & evidence

ORD record: ord-2834e23e93ab4fccb84621afcee5e172
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422279B2

Reaction notes

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