Water → 3-(2,6-Dichloro-4-hydroxybenzyl)-1-(cis-2-methylcyclohexyl)pyrrolidin-2-one

HRID 2235276Notes

Reaction equation

[Cl:1][C:2]1[CH:21]=[C:20]([O:22]C)[CH:19]=[C:18]([Cl:24])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[CH3:16])[C:6]1=[O:17].B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([Cl:24])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[CH3:16])[C:6]1=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 3-(2,6-dichloro-4-methoxybenzyl)-1-(cis-2-methylcyclohexyl) pyrrolidin-2-one (1.29 g, 3.47 mmol) in DCM (100 mL) and cool to 0° C. Stir the solution under N2 and add BBr3 (2.61 g, 10.42 mmol). Continue to stir the reaction mixture for 2 hours and add water (100 mL). Extract the aqueous layer with dichloromethane (3×200 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 40-100% of EtOAc-Hexane) to give 1.06 g (85%) of the title compound as a white solid: MS (APCI-pos mode) m/z (rel intensity) 356.1 (100), 358.1 (60).

Workup

stirringContinue to stir the reaction mixture for 2 hours
extractionExtract the aqueous layer with dichloromethane (3×200 mL)
dry with materialCombine the organic layers and dry with Na2SO4
filtrationfilter
concentrationconcentrate
custompurify by flash column chromatography (silica gel, 40-100% of EtOAc-Hexane)

Sources & evidence

ORD record: ord-9602f50ab682406daff92a760d6ed79f
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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