Benzyltriphenylphosphonium bromide → 1-(4-Methoxy-benzenesulfonyl)-3-styryl-azepane-2-carboxylic acid tert-butyl ester

HRID 1872239Notes

Reaction equation

HRID 1872239 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.[C:33]([O:37][C:38]([CH:40]1[CH:46]([CH:47]=O)[CH2:45][CH2:44][CH2:43][CH2:42][N:41]1[S:49]([C:52]1[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=1)(=[O:51])=[O:50])=[O:39])([CH3:36])([CH3:35])[CH3:34]>C1COCC1.CCCCC>[C:33]([O:37][C:38]([CH:40]1[CH:46]([CH:47]=[CH:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:45][CH2:44][CH2:43][CH2:42][N:41]1[S:49]([C:52]1[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=1)(=[O:51])=[O:50])=[O:39])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 2734970Benzyltriphenylphosphonium bromideHCID 539203363-Formyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

Product 1

HCID 543754621-(4-Methoxy-benzenesulfonyl)-3-styryl-azepane-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Benzyl triphenylphosphonium bromide (229 mg, 0.528 mmoL) in 2 mL of THF at 0° C. was added 2.0M butyl lithium solution (0.272 mL) in pentane. After five minutes the solution was warmed to ambient temperature, and kept at that temperature for 30 minutes before adding in the 3-Formyl-1-(4-methoxy-benzene sulfonyl)-azepane-2-carboxylic acid tert-butyl ester (200 mg, 0.503 mmoL) dissolved in 1.52 mL of THF. After 20 hours the reaction was quenched by adding water dropwise, the reaction was diluted with ethyl acetate and washed twice with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The residue was purified by column chromatography (silica: 20% to 25% ethyl acetate in hexanes) to yield 1-(4-Methoxy-benzenesulfonyl)-3-styryl-azepane-2-carboxylic acid tert-butyl ester; MS: (M+H)+ =472, (M+NH4)+ =489.

Workup

  1. customAfter 20 hours the reaction was quenched
  2. additionby adding water dropwise
  3. additionthe reaction was diluted with ethyl acetate
  4. washwashed twice with brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe residue was purified by column chromatography (silica: 20% to 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7bf6c12f07b04891b7a437a40cf5538e
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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