Hydrochloric Acid → (1R,3S,5R)-2-tert-butoxycarbonyl-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

HRID 1527428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527428
C([O:3][C:4]([C@@H:6]1[CH2:11][C@:10]2([CH3:12])[C@@H:8]([CH2:9]2)[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:5])C.[OH-].[K+].Cl.C(Cl)Cl>CO.C1COCC1.O>[C:16]([O:15][C:13]([N:7]1[C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][C@:10]2([CH3:12])[C@H:8]1[CH2:9]2)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 68283670HCID 68283670, Verbindung

Produkt 1

HCID 58384672(1R,3S,5R)-2-tert-butoxycarbonyl-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (185 mg, 0.69 mmol) in MeOH (1.1 mL), THF (1.1 mL) and H2O (1.1 mL) was added KOH (77 mg, 1.37 mmol). The solution was stirred 2.5 h at RT, HCl (0.1N) was added (until pH 1), CH2Cl2 was added and the layers were separated (×2). The combined organic layers were dried (Na2SO4), filtered and concentrated. The material (yellow oil) thus obtained was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.46 (m, 1H), 3.86 (m, 1H), 3.06 (m, 1H), 2.40 (dd, 1H), 1.86 (m, 1H), 1.37 (m, 9H), 1.18 (s, 3H) 0.65 (m, 2H).

Aufarbeitung

  1. additionwas added
  2. customthe layers were separated (×2)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material (yellow oil) thus obtained
  7. customwas used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-4a27fc7669864962a2d908a7659c6fda
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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