1,8-Diazabicyclo(5.4.0)undec-7-ene → ((1R,4S)-4-azidocyclopent-2-enyl)benzene

HRID 2404376ノート

反応式

HRID 2404376 の反応式
[C:1]1([C@@H:7]2[CH2:11][C@@H:10](O)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P([N:27]=[N+:28]=[N-:29])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.O>[N:27]([C@H:10]1[CH2:11][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9]1)=[N+:28]=[N-:29]

参加物

6

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 13613834(1R,4R)-4-phenylcyclopent-2-enol

生成物 1

HCID 130951056((1R,4S)-4-azidocyclopent-2-enyl)benzene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

A solution of Example 48A (458 mg, 2.86 mmol) and toluene (4.6 mL) was cooled to <5° C. and diphenylphosphoryl azide (0.740 mL, 3.43 mmol) and DBU (0.603 mL, 4.00 mmol) were added. After 5 hours at room temperature, LCMS showed complete reaction. Water (20 mL) and toluene (50 mL) were added and organic layer was washed with water (20 mL), 2N HCl (20 mL), and brine (10 mL) sequentially. The organic layer was dried (Na2SO4), filtered, and concentrated, and crude title compound was used in the next step. MS (DCI) m/z 203 (M+NH4)+.

後処理

  1. customreaction
  2. washorganic layer was washed with water (20 mL), 2N HCl (20 mL), and brine (10 mL) sequentially
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-edc93e35cb4d42dba51d0a2d39640094
出典データセット
uspto-grants-2014_08
特許番号
US08802711B2

反応ノート

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