trans-1-Boc-4-aminomethyl-3-hydroxypiperidine → HCID 11015727, Verbindung

HRID 353342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353342
[NH2:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][C@H:4]1[OH:16].[NH2:17][C:18]1[C:30]([Cl:31])=[CH:29][C:21]([C:22](N2C=CN=C2)=[O:23])=[C:20]([O:32][CH3:33])[C:19]=1[O:34][CH3:35]>C(#N)C>[NH2:17][C:18]1[C:30]([Cl:31])=[CH:29][C:21]([C:22]([NH:1][CH2:2][C@@H:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:5][C@H:4]2[OH:16])=[O:23])=[C:20]([O:32][CH3:33])[C:19]=1[O:34][CH3:35]

Komponenten

4

Edukt 2

HCID 11075229trans-1-Boc-4-aminomethyl-3-hydroxypiperidineHCID 88040818HCID 88040818, Verbindung

Produkt 1

HCID 11015727HCID 11015727, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of intermediate (1-e) (0.087 mol) and intermediate (3-a) (0.087 mol) in acetonitrile (600 ml) was stirred and refluxed for 90 min. The reaction mixture was cooled, and the solvent was evaporated. The residue was partitioned between DCM and water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was suspended in DIPE with a drop of ACN, filtered off and dried (vacuum, 40° C.), yielding 30.3 g (80%) of (±)-1,1-dimethylethyl trans-4-[[(4-amino-5-chloro-2,3-dimethoxybenzoyl)amino]methyl]-3-hydroxy-1-piperidinecarboxylate (interm. 4).

Aufarbeitung

  1. temperaturerefluxed for 90 min
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was evaporated
  4. customThe residue was partitioned between DCM and water
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. filtrationfiltered off
  10. customdried (vacuum, 40° C.)

Quellen und Nachweise

ORD-Eintrag
ord-f649c2ede5634f988e45339bcfac2953
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750349B2

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