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Pyrrolidine → (R)-tert-butyl 2-(pyrrolidine-1-carbonyl)morpholine-4-carboxylate

HRID 931316
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 931316
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][O:35][C@@H:34]([C:38]([OH:40])=O)[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N(C(C)C)CC)(C)C.N1CCCC1>ClCCl>[N:13]1([C:38]([C@@H:34]2[O:35][CH2:36][CH2:37][N:32]([C:30]([O:29][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:31])[CH2:33]2)=[O:40])[CH2:14][CH2:15][CH2:16][CH2:11]1
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Komponenten

6

Edukt 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 6559076(2R)-4-((tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 117966471(R)-tert-butyl 2-(pyrrolidine-1-carbonyl)morpholine-4-carboxylate
Ausbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HATU) (1.47 g, 4.3 mmol) was added to a solution of (R)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (1 g, 4.3 mmol) and diisopropylethylamine (1.11 g, 8.6 mmol) in anhydrous dichloromethane (20 mL) at room temperature. Pyrrolidine (0.45 mL, 5.62 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The mixture was partitioned between water and dichloromethane. The organics were dried over sodium sulfate and concentrated under reduced pressure and the resulting residue was purified via column chromatography (100-200 mesh silica gel, 0-0.5% methanol in dichloromethane) to afford (R)-tert-butyl 2-(pyrrolidine-1-carbonyl)morpholine-4-carboxylate (0.62 g).

Aufarbeitung

  1. customThe mixture was partitioned between water and dichloromethane
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified via column chromatography (100-200 mesh silica gel, 0-0.5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-45286df1fb8b40ff86464aaf57037ec6
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296745B2

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