Pyrrolidine → cis-Tert-butyl 4-methyl-3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate

HRID 931304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931304
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][C@H:49]([CH3:52])[C@H:48]([C:53](O)=[O:54])[CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40]>ClCCl>[CH3:52][C@H:49]1[CH2:50][CH2:51][N:46]([C:44]([O:43][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:45])[CH2:47][C@H:48]1[C:53]([N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:54]

Komponenten

6

Edukt 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86317483(3S,4S)-1-Boc-4-methyl-piperidine-3-carboxylic acid

Produkt 1

HCID 131735165cis-Tert-butyl 4-methyl-3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HATU) (4.12 g, 10.85 mmol), diisopropylethylamine (2.33 g, 18.08 mmol) and pyrrolidine (782 mg, 10.85 mmol) were added to a solution of cis-1-(tert-butoxycarbonyl)-4-methylpiperidine-3-carboxylic acid (2.2 g, 9.04 mmol) in anhydrous dichloromethane (30 mL) at room temperature. The reaction mixture was stirred at room temperature for 4 h. The mixture was quenched with water and was extracted with dichloromethane. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford cis-tert-butyl 4-methyl-3-(pyrrolidine-1-carbonyl)piperidine-1-carboxylate (2.6 g).

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionwas extracted with dichloromethane
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f2c9be0abc144677bb4e622def6916f5
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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