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

HRID 350342ノート

反応式

HRID 350342 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-95c0a3a4b56e48b98047494a3a4bc857
出典データセット
uspto-grants-2007_02
特許番号
US07179819B2

反応ノート

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