Sodium borohydride → N-[4-((1R)-1-{[(R)-tert-butylsulfinyl]amino}ethyl)-2-methylphenyl]methanesulfonamide

HRID 230585

Reaktionsgleichung

Reaktionsgleichung von HRID 230585
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:6]([CH3:15])[CH:5]=1)(=O)[CH3:2].[CH3:16][C:17]([S@:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].[BH4-].[Na+]>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:17]([S@:20]([NH:22][C@@H:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:6]([CH3:15])[CH:5]=1)[CH3:2])=[O:21])([CH3:19])([CH3:18])[CH3:16]

Komponenten

6

Edukt 3

HCID 4311764Sodium borohydrideHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 19873430N-(4-Acetyl-2-methylphenyl)methanesulfonamide

Produkt 1

HCID 58640404N-[4-((1R)-1-{[(R)-tert-butylsulfinyl]amino}ethyl)-2-methylphenyl]methanesulfonamideAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76524Titanium tetraethoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of titanium(IV) ethoxide (1.32 g, 5.8 mol) and N-(4-acetyl-2-methylphenyl) methanesulfonamide (800 mg, 3.5 mmol) in tetrahydrofuran (20 mL) was added (R)-(+)-2-methyl-2-propanesulfinamide (423 mg, 350 mmol) under a nitrogen atmosphere and the mixture was heated at 70° C. for 16 hours. It was quenched with water and the resulting white precipitate was filtered off. The filtrate was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with hexane/ethyl acetate (4:1). The yellow oil obtained was dissolved in tetrahydrofuran (10 mL) and the solution was added to sodium borohydride (242 mg, 6.4 mmol) in tetrahydrofuran (10 mL) at −70° C. The mixture was stirred at −70° C. for 5 hours and then quenched with methanol. It was stirred at room temperature for 1 hour and concentrated in vacuo to furnish 530 mg (45%) of the title compound. MS (ESI) m/z 333 (M+H)+, 331 (M−H)−.

Aufarbeitung

  1. customIt was quenched with water
  2. filtrationthe resulting white precipitate was filtered off
  3. customThe filtrate was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with hexane/ethyl acetate (4:1)
  8. customThe yellow oil obtained
  9. customquenched with methanol
  10. stirringIt was stirred at room temperature for 1 hour
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7919c91fd68a426cb45669c1a7f2747c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566739B2

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