Boron trifluoride etherate → (3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol

HRID 1087618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087618
[BH4-].[Na+].B(F)(F)F.CCOCC.[C:12]1([CH3:30])[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:28][CH:27]([OH:29])[CH2:26][C@H:22]2[C:23](O)=[O:24])(=[O:20])=[O:19])=[CH:14][CH:13]=1>O1CCCC1>[OH:24][CH2:23][C@@H:22]1[CH2:26][C@@H:27]([OH:29])[CH2:28][N:21]1[S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:30])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 211404091-(4-Toluenesulfonyl)-4-hydroxy-L-proline

Produkt 1

HCID 11265723(3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-olAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 2 1 of tetrahydrofuran (THF) was added 57.6 g (1523 mmol) of sodium borohydride and the mixture was cooled to 10° C. before 250 ml (1980 mmol) of borontrifluoride etherate was added dropwise over a period of 1 hour. Then 215.3 g (755.4 mmol) of 1-(4-toluenesulfonyl)-4-hydroxy-L-proline was added carefully in 100 ml of THF and the mixture was allowed to stir for 16 hours. The reaction was quenched with methanol and 10% aqueous hydrogen chloride solution was added and the mixture was gently heated to 60° C. for 1 hour. The reaction mixture was filtered and the pH was adjusted to neutral with 50% aqueous sodium hydroxide solution and the volatiles were evaporated under reduced pressure. The product was then isolated via filtration and the filter cake was washed with water. Drying under vacuum at 60° C. for 12 hours yielded 164 g of the product as a white solid in 85 % yield. M.P. 132°-133° C.

Aufarbeitung

  1. additionwas added dropwise over a period of 1 hour
  2. customThe reaction was quenched with methanol and 10% aqueous hydrogen chloride solution
  3. additionwas added
  4. filtrationThe reaction mixture was filtered
  5. customthe volatiles were evaporated under reduced pressure
  6. customThe product was then isolated via filtration
  7. washthe filter cake was washed with water
  8. customDrying under vacuum at 60° C. for 12 hours

Quellen und Nachweise

ORD-Eintrag
ord-830e910c920e4c35bfa4e90752b80a72
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05036153

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