Ytterbium → tert-Butyl piperazine-1-carboxylate

HRID 891049

Reaktionsgleichung

Reaktionsgleichung von HRID 891049
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[CH:15]=1.[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[Yb]>C(Cl)Cl>[CH3:14][C:12]1[S:13][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][CH3:17])=[CH:15][C:10]=2[N:11]=1.[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1

Komponenten

6

Edukt 3

HCID 23992YtterbiumHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23598944HCID 23598944, Verbindung

Produkt 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 69622255HCID 69622255, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-[((2S)oxiran-2-yl)methoxy]-2-methylbenzothiazole, a compound of formula (3) (6.2 g, 28 mmol), and tert-butyl 1-piperazinecarboxylate, a compound of formula (4) (5.7 g, 31 mmol), in methylene chloride (200 ml), was added ytterbium (111) trifluoromethanesulfonate (1.73 g, 28 mmol). The resulting solution was allowed to stir at room temperature overnight. The solvent was evaporated (in vacuo), to yield a semi-solid, which was chromatographed on silica gel, eluting with 5% methanol/methylene chloride, to yield (2S)-1-(2-methylbenzothiazol-5-yloxy)butan-2-ol, tert butyl piperazinecarboxylate as a clear oil (9.5 g, 23 mmol).

Aufarbeitung

  1. customThe solvent was evaporated (in vacuo)
  2. customto yield a semi-solid, which
  3. customwas chromatographed on silica gel
  4. washeluting with 5% methanol/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-d33019e973ea4497a1d6185fb865729b
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001909B2

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