Tetrabutylammonium borohydride → HCID 19900822, compound

HRID 2081804Notes

Reaction equation

HRID 2081804 reaction equation
[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([N:22]1[C:30]2[C:25](=[CH:26][C:27]([S:31]([CH2:34][N+:35]([O-:37])=[O:36])(=[O:33])=[O:32])=[CH:28][CH:29]=2)[CH2:24][CH2:23]1)(=O)[CH3:20]>ClCCl>[CH2:19]([N:22]1[C:30]2[C:25](=[CH:26][C:27]([S:31]([CH2:34][N+:35]([O-:37])=[O:36])(=[O:32])=[O:33])=[CH:28][CH:29]=2)[CH2:24][CH2:23]1)[CH3:20]

Participants

4

Reactant 2

HCID 169536Tetrabutylammonium borohydrideHCID 19780710HCID 19780710, compound

Product 1

HCID 19900822HCID 19900822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetrabutylammonium borohydride (3.85 g, 15 mM) was added to a solution of 1-acetyl-5-(nitromethylsulphonyl)indoline (1.45 g, 5 mM) in dichloromethane (30 ml), and the mixture was stirred at reflux for 18 hours. The solvent was removed by evaporation, 2M hydrochloric acid (30 ml) was added, and the mixture was heated at reflux for 20 minutes. The solution was then poured into sufficient of an ice-cold saturated solution of sodium hydrogen carbonate to adjust the mixture to pH 6. The mixture was then extracted with dichloromethane, the combined extracts were dried (MgSO4), and the solvent was removed by evaporation. The resultant yellow oil was purified by vacuum flash chromatography on silica, eluting with dichloromethane, to give 1-ethyl-5-(nitromethylsulphony)indoline as a solid, m.p. 122° C.; NMR (d6 -DMSO): 1.1(3H,t), 3.0(2H,t), 3.3(2H,m), 3.6(2H,t), 6.3(2H,s), 6.6(1H,d), 7.4(1H,d), 7.5(1H,dd); microanalysis, found: C,49.3; H,5.1; N,10.4%; C11H14N2O4S requires: C,48.9; H,5.2; N,10.4%.

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent was removed by evaporation, 2M hydrochloric acid (30 ml)
  3. additionwas added
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 20 minutes
  6. additionThe solution was then poured into sufficient of an ice-cold saturated solution of sodium hydrogen carbonate
  7. extractionThe mixture was then extracted with dichloromethane
  8. dry with materialthe combined extracts were dried (MgSO4)
  9. customthe solvent was removed by evaporation
  10. customThe resultant yellow oil was purified by vacuum flash chromatography on silica
  11. washeluting with dichloromethane

Sources & evidence

ORD record
ord-e2b4fb9c526040fcb7be08e8ec2d30ac
Source dataset
uspto-grants-1993_02
Patent number
US05185452

Reaction notes

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