Diazald → 2-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-methoxypiperidine-2,3-dicarboxylate

HRID 61471

Reaktionsgleichung

Reaktionsgleichung von HRID 61471
[N+](=[CH2:3])=[N-].CC1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[CH2:18]([N:25]1[CH2:30][C@@H:29]([OH:31])[CH2:28][C@H:27]([C:32]([O:34][CH3:35])=[O:33])[C@H:26]1[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCOCC>[CH2:18]([N:25]1[CH2:30][C@@H:29]([O:31][CH3:3])[CH2:28][C@H:27]([C:32]([O:34][CH3:35])=[O:33])[C@H:26]1[C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 6628DiazaldHCID 9550DiazomethaneHCID 866214902-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate

Produkt 1

HCID 1317319302-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-methoxypiperidine-2,3-dicarboxylateAusbeute 3,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Diazomethane was generated (from 5 g of Diazald) and distilled together with ether into a mixture of 2-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate (0.60 g, 0.0016 mol) and around 1 g of silica gel in 10 mL of ether. After distillation, the mixture was stirred at rt overnight. The mixture was diluted with methylene chloride, filtered to remove silica gel. The filtration was concentrated to dry and the resulting residue was applied on column, eluting with 0 to 40% EtOAc in Hexane, to yield the methyl ether compound (20 mg, 3.2%). MS (ESI): (M+H)+=398.1.

Aufarbeitung

  1. distillationAfter distillation
  2. additionThe mixture was diluted with methylene chloride
  3. filtrationfiltered
  4. customto remove silica gel
  5. filtrationThe filtration
  6. concentrationwas concentrated
  7. customto dry
  8. washeluting with 0 to 40% EtOAc in Hexane

Quellen und Nachweise

ORD-Eintrag
ord-d6b50734fdab42abaef84eeb7dbd4c9d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440958B2

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