Triethylamine → (3S)-3-(3-Chlorophenyl)cyclopentanone

HRID 1624031Notes

Reaction equation

HRID 1624031 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[C:11]1(=[O:16])[CH2:15][CH2:14][CH:13]=[CH:12]1.C(N(CC)CC)C>O1CCOCC1.O.[B-](F)(F)(F)F.C1C2C=CC1C=C2.C1C2C=CC1C=C2.[Rh].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:13]2[CH2:14][CH2:15][C:11](=[O:16])[CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 135882-Cyclopenten-1-oneHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 39239289(3S)-3-(3-Chlorophenyl)cyclopentanoneYield 89.2%

Reagents, catalysts & solvents 4

HCID 634876Binap, (A+-)-CatalystHCID 10915722Bis(norbornadiene)rhodium(I) tetrafluoroborateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Bis(norbornadiene)rhodium(I)tetrafluoroborate (0.20 g, 0.53 mmol) and (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (0.30 g, 0.48 mmol) are dissolved 1,4-dioxane (18 mL). The solution is degassed with nitrogen for 2 hours. 3-Chlorophenylboronic acid (4.95 g, 31.67 mmol) is dissolved in dioxane (24 mL) and water (6 mL). The mixture is degassed for another 2 hours. The two solutions are combined and stirred for two hours under a nitrogen stream. 2-Cyclopentenone (2.0 g, 24.36 mmol) and triethylamine (2.1 mL, 15.07 mmol) are added to the reaction sequentially, via syringe. This is stirred until completion under a stream of nitrogen. The reaction is filtered through a pad of diatomaceous earth and concentrated in vacuo. The residue is purified via silica gel flash chromatography, eluting with 20% ethyl acetate in hexane to give the title compound (4.23 g, 89.2%) as a clear, yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.9 (1H, M), 2.25 (2H, M), 2.45 (2H, M), 2.65 (1H, M), 3.35 (1H, M), 7.1 (1H, D), 7.25 (3H, M).

Workup

  1. customThe solution is degassed with nitrogen for 2 hours
  2. customThe mixture is degassed for another 2 hours
  3. stirringThis is stirred until completion under a stream of nitrogen
  4. filtrationThe reaction is filtered through a pad of diatomaceous earth
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified via silica gel flash chromatography
  7. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-850483ecb4834d338f44469f4360638b
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

Loading…