Water → 3-[5'-{[pyrrolidin-1-yl]sulfonyl}-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl]-2-bromo-butane

HRID 853920Notes

Reaction equation

HRID 853920 reaction equation
CC(C)([O-])C.[K+].[N:7]1([S:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[C:18]23[O:29][CH2:28][CH2:27][CH2:26][O:25]2)(=[O:14])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:31][CH2:32][CH:33]([Br:35])[CH3:34].O>CS(C)=O>[N:7]1([S:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH:32]([CH3:31])[CH:33]([Br:35])[CH3:34])[C:19](=[O:24])[C:18]23[O:29][CH2:28][CH2:27][CH2:26][O:25]2)(=[O:13])=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 78891,3-DibromobutaneHCID 23665647Potassium tert-butoxideHCID 589325715'-(pyrrolidin-1-ylsulfonyl)spiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one

Product 1

HCID 694104233-[5'-{[pyrrolidin-1-yl]sulfonyl}-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl]-2-bromo-butane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of potassium t-butoxide (0.12 g, 1 mmol, 1 eq) in anhydrous DMSO (5 mL) at room temperature under dry N2 atmosphere was added 5′-{[pyrrolidin-1-yl]sulfonyl}spiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one (previously described in step 2, Example 12) (0.33 g, 1 mmol). After stirring for 10 minutes, 1,3-dibromobutane (0.22 g, 1 mmol, 1 eq) was added dropwise to the reaction over a 5 minute period. The reaction mixture was stirred at room temperature for one hour. The mixture was poured into H2O (20 ml) and exhaustively extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel using 30% EtOAc/hexane to give the title compound as an off white solid (0.23 g, 50% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (API-ES+) m/z 474 [M+H].

Workup

  1. stirringThe reaction mixture was stirred at room temperature for one hour
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel using 30% EtOAc/hexane

Sources & evidence

ORD record
ord-0dc42e5b1fb64fdc92897db55330803c
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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