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

HRID 350342Notes

Reaction equation

HRID 350342 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 23511723[N-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyl 3-iodophenyl sulfideYield 45.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-95c0a3a4b56e48b98047494a3a4bc857
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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