HCID 58762434, compound → HCID 58762453, compound

HRID 1453008Notes

Reaction equation

HRID 1453008 reaction equation
[CH:1]1([Mg]Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1S[C:15](=[O:24])[CH2:16][CH2:17][C:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1>CCOCC.C1COCC1>[C:18]1([CH2:17][CH2:16][C:15]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

Participants

5

Reactant 2

HCID 58762434HCID 58762434, compoundHCID 178419650HCID 178419650, compound

Product 1

HCID 58762453HCID 58762453, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Cyclopentylmagnesium bromide (1.6 mL, 3.15 mmol, 2M soln in ether) was added to a cooled −78° C. solution of 3-Cyclohex-1-enyl-thiopropionic acid S-pyridin-2-yl ester (0.65 g, 2.63 mmol, from Step 3) dissolved in THF (10 mL). The reaction mixture was stirred for 45 min at −78° C. and then warmed up to rt. The reaction was quenched with 1N HCl and extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (0% to 5% EtOAc in hexanes) to give the title compound as a clear oil (0.39 g, 72%). 1H NMR (CDCl3): δ 1.51-1.83 (br m, 12H), 1.91 (m, 2H), 1.97 (m, 2H), 2.20 (t, 2H, J=7.6 Hz), 2.54 (t, 2H, J=7.8 Hz), 2.87 (m, 1H), 5.39 (s, 1H).

Workup

  1. temperaturewarmed up to rt
  2. customThe reaction was quenched with 1N HCl
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0% to 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2872d36e85d140009ee7c5b5a2d711bd
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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