Potassium Hydroxide → [N-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyl 3-iodophenyl sulfide

HRID 350342

Reaktionsgleichung

Reaktionsgleichung von HRID 350342
[I:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(O[CH2:19][CH:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])(=O)=O)=CC=1.[OH-].[K+]>N1C=CC=CC=1.CCOC(C)=O>[I:1][C:2]1[CH:3]=[C:4]([S:8][CH2:19][CH:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 13110388tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylateHCID 1372136052274-10-9

Produkt 1

HCID 23511723[N-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyl 3-iodophenyl sulfideAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred mixture of m-iodothiophenol (2.67 g, 11.31 mmol) and N-(tert-butoxy carbonyl)-2-pyrrolidinylmethyl p-toluenesulfonate (3.34 g, 9.43 mmol) in pyridine (9.4 mL) was added 8 N KOH (1.77 mL). The resulting mixture was stirred at room temp overnight. The reaction mixture was diluted with EtOAc. The solution was washed with H2O, sat. NH4Cl solution, brine, and dried over Na2SO4. The organic layer was concentrated under a reduced pressure and the residue was chromatographed on silica-gel with n-hexane-EtOAc (5:1, v/v) as eluent to afford 1.79 g (45%) [N-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyl 3-iodophenyl sulfide as an oil. 1H-NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 1.78–2.01 (br m, 4H), 2.71 (dt, 1H), 3.32–3.49 (br m, 3H), 3.90–4.02 (br m, 1H), 7.12 (d, J=7.8 Hz, 1H), 7.18 (d, J=7.8 Hz, 1H), 7.57 (dd, J=2.0, 8.3 Hz, 2H); MS (FAB) m/z 420 (M++1).

Aufarbeitung

  1. washThe solution was washed with H2O, sat. NH4Cl solution, brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe organic layer was concentrated under a reduced pressure
  4. customthe residue was chromatographed on silica-gel with n-hexane-EtOAc (5:1

Quellen und Nachweise

ORD-Eintrag
ord-95c0a3a4b56e48b98047494a3a4bc857
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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