4-Toluenesulfonyl chloride → (R)-3-tosyloxymethyl-1-methylpiperidine

HRID 1384974

Reaktionsgleichung

Reaktionsgleichung von HRID 1384974
[OH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH3:9])[CH2:4]1.[S:10](Cl)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11]>ClCCl>[S:10]([O:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH3:9])[CH2:4]1)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 920113(R)-(1-methylpiperidin-3-yl)methanol

Produkt 1

HCID 15895222(R)-3-tosyloxymethyl-1-methylpiperidineAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (R)-3-hydroxymethyl-1 -methylpiperidine (2.6 g, 20 mmol) in dichloromethane (70 mL) was cooled to 5° C. and tosyl chloride (3.8 g, 20 mmol) was added in portions during 15 minutes. After the addition was complete, the reaction was allowed to warm to room temperature and was stirred for 20 hours. The reaction mixture was then concentrated and the residue partitioned between 10% potassium hydroxide (50 mL) and ether (100 mL). The ether layer was removed and the aqueous phase extracted once again with ether (50 mL). The combined ether layers were dried over magnesium sulfate and concentrated to afford (R)-3-tosyloxymethyl-1 -methylpiperidine as a white solid (2.4 g, 42%), m.p. 74.5-81.0° C.

Aufarbeitung

  1. additionAfter the addition
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue partitioned between 10% potassium hydroxide (50 mL) and ether (100 mL)
  4. customThe ether layer was removed
  5. extractionthe aqueous phase extracted once again with ether (50 mL)
  6. dry with materialThe combined ether layers were dried over magnesium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-109302689e704cf1a2f324624ab9d0fb
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06262078B1

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