Ammonium Chloride → HCID 17917865, Verbindung

HRID 73556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73556
[CH:1]12[O:7][CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2]2.[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+]>CO.O>[N:18]([CH:1]1[CH:6]([OH:7])[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:2]1)=[N+:19]=[N-:20].[N:18]([CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:2][CH:1]1[OH:7])=[N+:19]=[N-:20]

Komponenten

7

Edukt 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13186888Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Produkt 2

HCID 17917865HCID 17917865, VerbindungHCID 59455704HCID 59455704, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (1.0 equiv.) in MeOH and water (0.17M) was added sodium azide (2.0 equiv.) and ammonium chloride (1.0 equiv.). The reaction was stirred at 65° C. in an oil bath for 7 h, then concentrated to remove the methanol. Ethyl acetate was added, the organic phase was separated, dried with Na2SO4, and concentrated under vacuo to give benzyl 3-azido-4-hydroxypiperidine-1-carboxylate and benzyl 4-azido-3-hydroxypiperidine-1-carboxylate as a clear oil in >95% yield. LCMS (m/z): 276.9 (MH+), Rt=2.98 min.

Aufarbeitung

  1. concentrationconcentrated
  2. customto remove the methanol
  3. additionEthyl acetate was added
  4. customthe organic phase was separated
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9d7c1e62238243e79ff875ecba2af36d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829193B2

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