Isopropyl iodide → 8-Oxo-2,2-dimethyl-7alpha-isopropyl-3-oxa-1-azabicyclo[4.2.0]octane

HRID 345240노트

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HRID 345240 반응식
[CH:1](NC(C)C)([CH3:3])[CH3:2].C([Li])CCC.[O:13]=[C:14]1[N:21]2[CH:16]([CH2:17][CH2:18][O:19][C:20]2([CH3:23])[CH3:22])[CH2:15]1.C(I)(C)C>CCCCCC.C1COCC1.CCOC(C)=O.CN(C)P(N(C)C)(N(C)C)=O>[O:13]=[C:14]1[N:21]2[CH:16]([CH2:17][CH2:18][O:19][C:20]2([CH3:23])[CH3:22])[CH:15]1[CH:1]([CH3:3])[CH3:2]

참가 물질

9

반응물 4

HCID 6362Isopropyl iodideHCID 7912DiisopropylamineHCID 12769229HCID 12769229, 화합물HCID 178418339Butyllithium

생성물 1

HCID 130511448-Oxo-2,2-dimethyl-7alpha-isopropyl-3-oxa-1-azabicyclo[4.2.0]octane

시약·촉매·용매 4

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
-78 °C

실험 절차

THF, 20 ml is placed under N2, treated with 1.54 ml diisopropylamine and cooled to -78° C. A solution of n-butyl lithium 1.97 M in hexane 5.6 ml is added dropwise over 5 min. The reaction mixture is stirred at -78° C. for 10 min and then treated with 8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane 1.55 g in 15 ml THF added dropwise over 5 min. After another 10 min hexamethylphosphoramide 1.97 ml is added. The mixture is stirred another 10 min, then treated with 2 ml of isopropyl iodide. The reaction mixture is stirred at -78° C. for 15 min and allowed to warm to 25° C. and stirred for 15 min. The reaction mixture is diluted with EtOAc, washed once with pH 7 phosphate buffer then dried and evaporated. The residue is chromatographed on silica gel using 25% EtOAc/C6H6 as eluant to give 8-oxo-2,2-dimethyl-7α-isopropyl-3-oxa-1-azabicyclo[4.2.0]-octane.μ i.r.: 5.7 (β-lactam).

후처리

  1. additionadded dropwise over 5 min
  2. stirringThe mixture is stirred another 10 min
  3. stirringThe reaction mixture is stirred at -78° C. for 15 min
  4. temperatureto warm to 25° C.
  5. stirringstirred for 15 min
  6. washwashed once with pH 7 phosphate buffer
  7. customthen dried
  8. customevaporated
  9. customThe residue is chromatographed on silica gel using 25% EtOAc/C6H6 as eluant

출처 및 근거

ORD 기록
ord-a38c5daf776b4c1587a10983e46cb352
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05055573

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