Cyclopropylamine → HCID 45087015, Verbindung

HRID 859876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 859876
[CH2:1]([N:8]1[CH2:12][C@H:11]([CH3:13])[C@@H:10]([C:14]([OH:16])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1([NH2:20])[CH2:19][CH2:18]1.C(N=C=NCCCN(C)C)C.Cl>ClCCl>[CH2:1]([N:8]1[CH2:12][C@H:11]([CH3:13])[C@@H:10]([C:14]([NH:20][CH:17]2[CH2:19][CH2:18]2)=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 69828CyclopropylamineHCID 1515523trans-1-Benzyl-4-methyl-pyrrolidine-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 45087015HCID 45087015, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(3R,4R)-1-Benzyl-4-methyl-3-pyrrolidinecarboxylic acid (6.27 g) was suspended in dichloromethane (250 mL). To this suspension, cyclopropylamine (1.76 mL) and hydrochloric acid 1-ethyl-(3-dimethylaminopropyl)carbodiimide (12.2 g) were sequentially added and the mixture was stirred at room temperature for 4 hours. Subsequently, the reaction mixture was washed with water, was dried over anhydrous sodium sulfate, and was then concentrated under reduced pressure. The resulting residue was purified on a silica gel column (ethyl acetate: methanol=10:1) to give 3.32 g of (3R,4R)-1-benzyl-N-cyclopropyl-4-methyl-3-pyrrolidinecarboxamide as a white crystal.

Aufarbeitung

  1. washSubsequently, the reaction mixture was washed with water
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated under reduced pressure
  4. customThe resulting residue was purified on a silica gel column (ethyl acetate: methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-7c2e2d0048fd4424b6c5c657a59f4b0c
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153851B2

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