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

HRID 2404376노트

반응식

HRID 2404376 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-edc93e35cb4d42dba51d0a2d39640094
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802711B2

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