Tetrahydrofuran → HCID 59299517, compound

HRID 2235291Notes

Reaction equation

HRID 2235291 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][CH:11]1[CH2:15][CH2:14][N:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:12]1=[O:22])[C:5]#N.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C[O:34]CC1>>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([CH2:10][CH:11]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:12]2=[O:22])=[C:2]([Cl:1])[CH:3]=1)(=[O:34])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 59299333HCID 59299333, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 59299517HCID 59299517, compoundYield 9%

Procedure

Dissolve 3-chloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)benzonitrile (0.20 g, 0.63 mmol) in THF (20 mL) under N2 and add phenylmagnesium bromide (0.63 mL, 0.63 mmol, 1.0 M in THF). Stir the reaction mixture for 24 hours until LC-MS shows the starting material has gone. Add saturated NH4Cl (20 mL) and extract the aqueous with EtOAc (3×50 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 20-50% of EtOAc-Hexane) to give 0.023 g (9%) of the title compound as white solid: MS (APCI-pos mode) m/z (rel intensity) 396.3 (100), 398.2 (30).

Workup

  1. extractionAdd saturated NH4Cl (20 mL) and extract the aqueous with EtOAc (3×50 mL)
  2. dry with materialCombine the organic layers and dry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash column chromatography (silica gel, 20-50% of EtOAc-Hexane)

Sources & evidence

ORD record
ord-45ab8028a31f48068c93ea89e27dbc94
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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