Aluminium lithium hydride → 2-(2-(4-Chlorophenyl)-2,4,5,6-tetrahydrocyclopenta[C]pyrazol-3-YL)-2-cyclohexylethanol

HRID 889372Notes

Reaction equation

C([O:3][C:4](=O)[CH:5]([C:12]1[N:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:14]=[C:15]2[CH2:19][CH2:18][CH2:17][C:16]=12)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([N:13]2[C:12]([CH:5]([CH:6]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]3)[CH2:4][OH:3])=[C:16]3[CH2:17][CH2:18][CH2:19][C:15]3=[N:14]2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of [2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid ethyl ester (500 mg, 1.2 mmol) in THF (25 ml) was added within 20 min to an ice cold suspension of lithium aluminium hydride (66 mg, 1.7 mmol) in THF (25 ml). The solution was stirred at 0° C. for 45 min, filtered over Speedex and the filtrate was brought to dryness under reduced pressure. The residue was taken up in ice water/brine 1/1 and iPrOAc. The layers were separated and the aqueous layer was extracted one more time with iPrOAc. The combined extracts were dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give the title compound (336 mg, 0.97 mmol; 79%) as yellow oil which was used in the next step without further purification. MS: m/e=345.2 [M+H+].

Workup

filtrationfiltered over Speedex
customThe layers were separated
extractionthe aqueous layer was extracted one more time with iPrOAc
dry with materialThe combined extracts were dried over Na2SO4
filtrationAfter filtration the solvent
customwas removed under reduced pressure

Sources & evidence

ORD record: ord-2e62b7990462425f9e89ab41b7aa9e57
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252826B2

Reaction notes

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