1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 2'-fluoro-2-(5-methyl-2-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662454Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[CH:24](OS(C)(=O)=O)[CH2:23][CH2:22][CH:21]1[CH3:30].C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[CH:21]([CH3:30])[CH2:22][CH:23]=[CH:24]1

Participants

Conditions

Temperature: 95 °C

Procedure

A 200 mL round bottom flask was charged with 66.56E (mixture of diastereomers) (0.59 g, 1.4 mmol), toluene (10 mL), and DBU (2.0 mL, 14 mmol). The resulting solution was stirred for 16 hours at 95° C., cooled to room temperature, and quenched with 1 N HCl. The mixture was diluted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated. The initial product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford 66.56F (mixture of diastereomers) (0.31 g, 67% yield) as a colorless oil.

Workup

temperaturecooled to room temperature
customquenched with 1 N HCl
additionThe mixture was diluted with EtOAc
washwashed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe initial product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

Sources & evidence

ORD record: ord-dfc436f3cf014a5c8cd8972501b2e963
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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