1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-azido-3,4-dihydro-2H-pyrano[2,3-b]pyridine

HRID 1508191ノート

反応式

HRID 1508191 の反応式
[O:1]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[CH:4](O)[CH2:3][CH2:2]1.C1C=CC(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:26]([CH:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[O:1][CH2:2][CH2:3]1)=[N+:27]=[N-:28]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 230491373,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol

生成物 1

HCID 598465164-azido-3,4-dihydro-2H-pyrano[2,3-b]pyridine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a mixture of 3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol (3.31 mmol) in 16.5 mL toluene were added DPPA (4.96 mmol) followed by DBU (4.96 mmol) at 0° C. The cooling bath was removed after 2 h and the mixture was stirred at RT overnight. The reaction was quenched by adding sat. aq. NaHCO3 solution and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (4/1) to EtOAc gives the desired product as colorless oil;

後処理

  1. customThe cooling bath was removed after 2 h
  2. customThe reaction was quenched
  3. additionby adding sat. aq. NaHCO3 solution
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by CC (KP-SIL™ from Biotage)

出典と根拠

ORDレコード
ord-a391b02ed9834d7aac3e6b0926db75e4
出典データセット
uspto-grants-2015_12
特許番号
US09221832B2

反応ノート

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