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

HRID 1487510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487510
[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-aaad1549c40e4d0b96b29e1470909c0c
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428528B2

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