3-Hydroxypyridine → 1,1-Dimethylethyl (2R)-2-[(3-pyridinyloxy)methyl]-1-pyrrolidinecarboxylate

HRID 617284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 617284
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@@H:40]1[CH2:44][OH:45])=[O:38])([CH3:35])([CH3:34])[CH3:33].O[C:47]1[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=1>O1CCCC1>[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@@H:40]1[CH2:44][O:45][C:47]1[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33]

Komponenten

6

Edukt 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 688279N-(tert-Butoxycarbonyl)-D-prolinol

Produkt 1

HCID 107077241,1-Dimethylethyl (2R)-2-[(3-pyridinyloxy)methyl]-1-pyrrolidinecarboxylateAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of triphenylphosphine (1.24 g, 4.74 mmol) in 20 mL of tetrahydrofuran at room temperature was added diethyl azodicarboxylate (0.746 mL, 4.74 mmol) dropwise with stirring. After stirring at room temperature for 30 minutes, (R)-1-t-butoxycarbonyl-2-pyrrolidinemethanol (350 mg, 3.16 mmol) and 3-hydroxypyridine (450 mg, 4.74 mmol) were added to the reaction mixture. The resultant solution was then stirred at room temperature overnight. After all of the starting material was consumed, the organic solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography. Elution with chloroform:methanol (10:1) provided 518 mg of the title compound along with substantial amount of reduced DEAD reagent. MS (DCI/NH3) m/e 279 (M+H)+.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 30 minutes
  2. customAfter all of the starting material was consumed
  3. customthe organic solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washElution with chloroform:methanol (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-0e3543538ff442f7b91b1777c1534d6c
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948793

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