HCID 59577095, compound → HCID 59577325, compound

HRID 2041987Notes

Reaction equation

[C:1]([C:5]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=2)=[O:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:28][Mg]I>C(OCC)C>[C:1]([C:5]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])([CH3:28])[CH3:21])=[CH:16][CH:15]=2)=[O:13])[CH2:9]1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of 1-(4-(3-(2-tert-butyl-4-fluorophenoxy)azetidin-1-carbonyl)phenyl)ethanone (0.14 g, 0.37 mmol) in diethyl ether (2.0 mL) was added methyl magnesium iodide (0.25 mL, 3.0 M in diethyl ether, 0.75 mmol) dropwise at room temperature. The resulting reaction mixture was heated to reflux for 1.5 h. After this reaction mixture was cooled to 0° C., diluted with diethyl ether, quenched with 1 N hydrochloric acid (2 ml) and the reaction mixture was stirred until the solids disappeared. The organic layer was separated and washed with water (2×2.0 mL), dried (Na2SO4), filtered and the filtrate was directly purified by flash column chromatography (silica gel, 50:50 ethyl acetate/heptane) to provide (3-(2-tert-butyl-4-fluorophenoxy)azetidine-1-yl)(4-(2-hydroxypropan-2-yl)phenyl)methanone (0.081 g, 57%) as a white solid.

Workup

customThe resulting reaction mixture
temperaturewas heated
temperatureto reflux for 1.5 h
customquenched with 1 N hydrochloric acid (2 ml)
customThe organic layer was separated
washwashed with water (2×2.0 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
customthe filtrate was directly purified by flash column chromatography (silica gel, 50:50 ethyl acetate/heptane)

Sources & evidence

ORD record: ord-bfe94cb98cff4b948a791a0865540577
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586571B2

Reaction notes

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