Potassium Hydroxide → [N-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyl 4-iodophenyl sulfide

HRID 354281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354281
[I:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=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:7]=[CH:6][C:5]([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:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 6569004-Iodobenzene-1-thiolHCID 13110388tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 23511708[N-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyl 4-iodophenyl sulfideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred mixture of p-iodothiophenol (1.75 g, 7.43 mmol) and N-(tert-butoxycarbonyl)-2-pyrrolidinylmethyl p-toluenesulfonate (2.39 g, 6.75 mmol) in pyridine (12.7 mL) was added 8N KOH (1.27 mL) at room temp, and the resulting mixture was stirred for 4 hr at the same temp. The reaction mixture was diluted with EtOAc. The solution was washed with H2O, sat NH4Cl, brine, and dried over Na2SO4. The organic layer was concentrated under a reduced pressure. The residue was chromatographed on silica-gel with n-hexane-EtOAc (5:1, v/v) as eluent to afford 1.49 g (53%) [N-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyl 4-iodophenyl sulfide as a pale yellowish oil. 1H-NMR (400 MHz, CDCl3) δ(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, 1), 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
  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-ef7de1369ca7471d81d0f2cd92278176
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756378B2

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