Potassium Carbonate → (1R,2R)-2-Amino-1-(4-azido-phenyl)-3-fluoro-propan-1-ol

HRID 1520509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520509
[NH2:1][C@@H:2]([CH2:12][F:13])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1)[OH:4].[N-:14]=[N+:15]=[N-:16].[Na+].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O.O>[NH2:1][C@@H:2]([CH2:12][F:13])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([N:14]=[N+:15]=[N-:16])=[CH:7][CH:6]=1)[OH:4]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 145742L-ProlineHCID 86695458(1R,2R)-2-Amino-3-fluoro-1-(4-iodo-phenyl)-propan-1-ol

Produkt 1

HCID 86695457(1R,2R)-2-Amino-1-(4-azido-phenyl)-3-fluoro-propan-1-olAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 23503278(Methanesulfinyl)methane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To the stirred solution of (1R,2R)-2-Amino-3-fluoro-1-(4-iodo-phenyl)-propan-1-ol (1 g, 3.38 mmol) in dimethylsulfoxide:water (9:1, 10 mL) is added NaN3 (0.26 g, 3.99 mmol), Na-ascorbate (0.1 g, 0.50 mmol), CuSO4.5H2O (0.17 g, 0.68 mmol), L-proline (78 mg, 0.67 mmol), K2CO3 (93 mg 0.67 mmol) and resulting reaction mixture heated to 60° C. for 5 hours. Diluted with cold water and extracted with ethylacetate and washed with excess of water and brine. Organic layer dried over sodium sulphate and solvent is evaporated in vacuo to get the crude title compound (0.6 g, crude), used as such in next step. LC-MS (m/z): [M+H]=211.2.

Aufarbeitung

  1. customresulting
  2. customreaction mixture
  3. extractionextracted with ethylacetate
  4. washwashed with excess of water and brine
  5. dry with materialOrganic layer dried over sodium sulphate and solvent
  6. customis evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bba0fe90f26e47a890ef0a606617f0c2
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073894B2

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