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

HRID 1487510ノート

反応式

HRID 1487510 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 23503278(Methanesulfinyl)methane--water (1/1)溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aaad1549c40e4d0b96b29e1470909c0c
出典データセット
uspto-grants-2016_08
特許番号
US09428528B2

反応ノート

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