Cyclopentanone → HCID 59090746, Verbindung

HRID 29185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29185
[CH2:1]([C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:9]([OH:13])[CH2:10][NH:11][NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)(C)C>[CH2:1]([C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C@H:9]([OH:13])[CH2:10][NH:11][N:12]=[C:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 8452CyclopentanoneHCID 59090665tert-butyl N-[(1S,2R)-1-benzyl-3-hydrazino-2-hydroxypropyl]carbamate

Produkt 1

HCID 59090746HCID 59090746, VerbindungAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of tert-butyl N-[(1S,2R)-1-benzyl-3-hydrazino-2-hydroxypropyl]carbamate (500 mg, 1.695 mmol) in 5 mL of isopropanol under Argon was treated with cyclopentanone (180 μL, 2.034 mmol). After stirring for approximately 18 hours, the reaction solvent was removed in vacuo and the residue was triturated with diethylether. The slurry was filtered and the solid was dried under high vacuum to provide tert-butyl N-[(1S,2R)-1-benzyl-3-(2-cyclopentylidenhydrazino)-2-hydroxypropyl]carbamate (85 mg, 14%) as a white solid. H1-NMR (chloroform-D3) 1.34 (s, 9H), 1.54 (b, 2H), 1.73 (m, 2H), 1.83 (m, 2H), 2.22 (m, 2H), 2.35 (m, 2H), 2.90 (m, 1H), 3.02 (m, 1H), 3.14 (m, 1H), 3.38 (m, 1H), 3.64 (bm, 1H), 3.84 (bm, 1H), 4.52 (m, 1H), 7.25 (m, 5H). MS(APCI): 361(M+Na).

Aufarbeitung

  1. customthe reaction solvent was removed in vacuo
  2. customthe residue was triturated with diethylether
  3. filtrationThe slurry was filtered
  4. customthe solid was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dc0c7637ad52455c8faa1f088ac154a1
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419967B2

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