Triphenylphosphine → Tert-butyl 3-(pyridin-4-yloxy)azetidine-1-carboxylate

HRID 1021223노트

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HRID 1021223 반응식
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[N:13]1[CH:18]=[CH:17][C:16](O)=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(C)C=CC=CC=1>C1COCC1>[N:13]1[CH:18]=[CH:17][C:16]([O:1][CH:2]2[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]2)=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 178418642HCID 178418642, 화합물HCID 178459888HCID 178459888, 화합물2회

생성물 1

HCID 24902675Tert-butyl 3-(pyridin-4-yloxy)azetidine-1-carboxylate수율 88.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
55 °C

실험 절차

tert-Butyl 3-hydroxyazetidine-1-carboxylate (4.0 g) and pyridin-4-ol (1.8 g) were mixed with THF (50 ml), and triphenylphosphine (6.23 g) was added thereto. A 1.9 M DIAD/toluene solution (12.5 ml) was added dropwise, followed by stirring at 55° C. overnight. Triphenylphosphine (5 g) and a 1.9 M DIAD/toluene solution (10 ml) were added to the reaction mixture, followed by stirring at 55° C. overnight. The reaction mixture was concentrated under reduced pressure, and a liquid separation operation was carried out by the addition of EtOAc and 0.5 M hydrochloric acid. The aqueous layer was adjusted to a pH of around 10 by the addition of a 4 M aqueous NaOH solution, and extracted with CHCl3. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain tert-butyl 3-(pyridin-4-yloxy)azetidine-1-carboxylate (4.2 g).

후처리

  1. additionwas added
  2. stirringby stirring at 55° C. overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customa liquid separation operation
  5. additionwas carried out by the addition of EtOAc and 0.5 M hydrochloric acid
  6. additionThe aqueous layer was adjusted to a pH of around 10 by the addition of a 4 M aqueous NaOH solution
  7. extractionextracted with CHCl3
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

출처 및 근거

ORD 기록
ord-8d4a735f39184121af8cdc6c176dffd8
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716470B2

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