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

HRID 525577Notes

Reaction equation

HRID 525577 reaction equation
[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]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 145742L-ProlineHCID 86695458HCID 86695458, compound

Product 1

HCID 86695457(1R,2R)-2-Amino-1-(4-azido-phenyl)-3-fluoro-propan-1-olYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9364cb880c5a466eb71940d9db385ea5
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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