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Triethylamine → (S)-tert-Butyl 2-((tosyloxy)methyl)morpholine-4-carboxylate

HRID 556874
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 556874
[C:1]1(C)[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[OH:12][CH2:13][C@H:14]1[O:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.[CH2:27](N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[S:7]([O:12][CH2:13][C@H:14]1[O:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1)([C:2]1[CH:1]=[CH:6][C:5]([CH3:27])=[CH:4][CH:3]=1)(=[O:8])=[O:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 1512577tert-Butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate

Produkt 1

HCID 54043638(S)-tert-Butyl 2-((tosyloxy)methyl)morpholine-4-carboxylateAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridine
Katalysator
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Toluene suiphonyl chloride (0.513 g, 2.69 mmol) was added to a solution of (S)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (0.390 g, 1.79 mmol), triethylamine (0.50 mL, 3.59 mmol) and DMAP (cat.) in dichloromethane (11 mL). The reaction mixture was stirred for 24 h then diluted with dichloromethane (25 ml) and washed sequentially with water (25 mL) and 0.2M HCl (25 mL). The organic phase was dried (Na2SO4) and the solvent was removed in vacuo. The crude product was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexane (1/5), to give the title compound as a colourless solid (0.650 g, 97%).

Aufarbeitung

  1. washwashed sequentially with water (25 mL) and 0.2M HCl (25 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash column chromatography on silica gel
  5. washeluting with ethyl acetate/hexane (1/5)

Quellen und Nachweise

ORD-Eintrag
ord-ca75f430e0e647dcaceb6cf6356b981a
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08058045B2

Notizen zur Reaktion

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