L-Proline → 6-(methylsulfonyl)-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 645287Notes

Reaction equation

HRID 645287 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:23][O:24][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]3=[O:22].[CH3:25][S:26]([O-:28])=[O:27].[Na+].N1CCC[C@H]1C(O)=O>CS(C)=O.O.[Cu](I)I>[CH3:25][S:26]([C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:23][O:24][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]3=[O:22])(=[O:28])=[O:27]

Participants

7

Reactant 3

HCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 592634366-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)one

Product 1

HCID 592634206-(methylsulfonyl)-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 46%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-1′-pentylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.60 g, 1.55 mmol), sodium methanesulfinate (0.19 g, 1.86 mmol), copper iodide (0.03 g, 0.16 mmol), and L-proline (0.04 g, 0.31 mmol) in dimethyl sulfoxide (3.00 mL) was heated at 100° C. for 2 days under N2. The reaction mixture was diluted with water (50.0 mL) and extracted with ethyl acetate (4×15.0 mL). The combined organics was dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (ethyl acetate/hexane, 2/3) to give the title compound (0.03 g, 46%) as a light yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.46-7.48 (m, 1H), 7.38 (dt, 1H), 7.34 (dt, 1H), 7.13-7.02 (m, 2H), 6.94 (d, 1H), 6.86 (d, 1H), 5.03 (d, 1H), 4.78 (d, 1H), 3.87-3.64 (m, 2H), 3.02 (s, 3H), 1.79-1.68 (m, 2H), 1.41-1.32 (m, 4H), 0.90 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 176.1, 161.2, 142.6, 142.1, 135.4, 131.5, 129.5, 124.3, 124.0, 123.5, 120.7, 109.5, 109.0, 80.5, 57.7, 44.5, 40.6, 29.0, 27.1, 22.3, 14.0; MS (ES+) m/z 386.5 (M+1).

Workup

  1. extractionextracted with ethyl acetate (4×15.0 mL)
  2. dry with materialThe combined organics was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-66bf11ab924c476d9cc0432f36c778f2
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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