Lithium hydroxide, monohydrate → 2-(Tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

HRID 712803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712803
[CH:1]12[CH2:6][CH:5]1[CH2:4][C@H:3]([C:7]([O:9]CC)=[O:8])[N:2]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].O[Li].O>O1CCOCC1.O>[C:15]([O:14][C:12]([N:2]1[CH:3]([C:7]([OH:9])=[O:8])[CH2:4][CH:5]2[CH:1]1[CH2:6]2)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 58405350(3R)-2-tert-butyl 3-ethyl 2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

Produkt 1

HCID 213390052-(Tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acidAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a mixture of (3R)-2-tert-butyl 3-ethyl 2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate (D26) (diastereoisomer mixture) (3.4 g, 13.3 mmol) in dioxane (15 ml) and water (15 ml), LiOH H2O (2.2 g, 53 mmol). The mixture was stirret at RT for 18 h. Dioxane was evaporated off and water was washed with Et2O (2×40 ml) then the pH was adjusted to ˜4 by addition of citric acid and the resulting aqueous phase was extacted with DCM (200 ml), washed with water (20 ml), dried over Na2SO4 and evaporated in vacuo to afford the title compound (D27) (2.75 g) as diastereoisomer mixture with syn-anti ratio 10/2.

Aufarbeitung

  1. customDioxane was evaporated off
  2. washwater was washed with Et2O (2×40 ml)
  3. additionthe pH was adjusted to ˜4 by addition of citric acid
  4. washwashed with water (20 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4408db64c5b346ab9b81bdc033596f28
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181279B2

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