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

HRID 384714
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 384714
[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 sulphonyl 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-e2344e7844c04e1a91c8972ef82fb80f
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367658B2

Notizen zur Reaktion

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