Ammonium Chloride → Ethyl (1S,3R,4R)-3-azido-4-hydroxycyclohexane-1-carboxylate

HRID 546456노트

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HRID 546456 반응식
[O:1]1[C@H:7]2[C@@H:2]1[CH2:3][C@@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:6]2.[Cl-].[NH4+].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C)C=O>[N:15]([C@H:2]1[C@H:7]([OH:1])[CH2:6][CH2:5][C@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1)=[N+:16]=[N-:17]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 57416186Ethyl (1S,3S,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylate

생성물 1

HCID 57416187Ethyl (1S,3R,4R)-3-azido-4-hydroxycyclohexane-1-carboxylate수율 100.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
75 °C

실험 절차

Ethyl (1S,3S,4R)-3,4-epoxycyclohexane-1-carboxylate (41 g) was dissolved in N,N-dimethyl-formamide (300 ml), ammonium chloride (19.3 g) and sodium azide (23.5 g) were successively added at room temperature, and the mixture was then stirred at 75° C. for 13 hours. The reaction mixture was filtered, the filtrate was concentrated to distill off 400 ml of the solvent, the product captured by the filter was put in the residue, and water was added to dissolve the collected product. The solution was extracted with ethyl acetate. The resultant organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (51.5 g) as an oil.

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. distillationto distill off 400 ml of the solvent
  4. additionwas added
  5. dissolutionto dissolve the collected product
  6. extractionThe solution was extracted with ethyl acetate
  7. washThe resultant organic layer was washed with water and saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-21bd43fc714140d9964d864c81ca0bd9
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935824B2

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