4-Toluenesulfonyl chloride → 2-(P-Tolylsulfonyl)-6-oxa-2-azaspiro[2.5]octane

HRID 1023827

Reaktionsgleichung

Reaktionsgleichung von HRID 1023827
[NH2:1][C:2]1([CH2:8]O)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:1]2[C:2]3([CH2:7][CH2:6][O:5][CH2:4][CH2:3]3)[CH2:8]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18316484(4-Aminooxan-4-yl)methanol

Produkt 1

HCID 584326642-(P-Tolylsulfonyl)-6-oxa-2-azaspiro[2.5]octaneAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-aminotetrahydro-2H-pyran-4-methanol (16 g, 122 mmol) in dichloromethane (700 mL) was treated with triethylamine (85 mL, 610 mmol), p-toluenesulfonyl chloride (69.8 g, 366 mmol) and DMAP (1490 mg, 12.2 mmol) under nitrogen. After approximately 18 hours at room temperature, the reaction was filtered through a pad of silica gel. The filtrate was concentrated in vacuo then purified by chromatography on silica gel (5-20% EtOAc/hexane) to afford intermediate the title compound (12.5 g) as a white solid.

Aufarbeitung

  1. filtrationthe reaction was filtered through a pad of silica gel
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthen purified by chromatography on silica gel (5-20% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ea84956d101c43f9b291da8d044e5740
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722727B2

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