Aluminium lithium hydride → HCID 90460626, compound

HRID 1846250Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:22]2[N:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[N:25]=[C:24]([CH3:33])[C:23]=2[C:34](OCC)=[O:35])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1>O1CCCC1>[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:22]2[N:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[N:25]=[C:24]([CH3:33])[C:23]=2[CH2:34][OH:35])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a stirred mixture of LiAlH4 (136 mg, 3.58 mmol, 3.99 equiv) in anhydrous tetrahydrofuran (20 mL) maintained under nitrogen at −40° C. was added dropwise a solution of (R/S) ethyl 5-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylate (410 mg, 0.90 mmol, 1.00 equiv) in tetrahydrofuran (10 mL). The reaction mixture was stirred at −40° C. for 1 h and then quenched with saturated NH4Cl solution (0.2 mL). The solid material was removed by filtration and the filtrate was concentrated under vacuum. The residue was purified on a silica gel column eluted with 30-100% of ethyl acetate in petroleum ether to give 320 mg (86%) of (R/S) (5-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methanol as a colorless oil. LCMS (method D, ESI): RT=1.51 min, m/z=415.0 [M+H]+.

Workup

customquenched with saturated NH4Cl solution (0.2 mL)
customThe solid material was removed by filtration
concentrationthe filtrate was concentrated under vacuum
customThe residue was purified on a silica gel column
washeluted with 30-100% of ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-07b299318025409fa095f911b7b5f8c7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952026B2

Reaction notes

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