四氢呋喃 → HCID 178421572，化合物

HRID 1036392

反应方程式

HRID 1036392 反应方程式
[C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([C@:25]1([CH3:31])[CH2:29][O:28][C:27](=[O:30])[NH:26]1)[CH:19]=[CH:18]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[C:1]1([C@H:7]2[CH2:8][CH2:9][C@H:10]([O:13][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[CH:21]=[C:20]([C@:25]3([CH3:31])[CH2:29][O:28][C:27](=[O:30])[NH:26]3)[CH:19]=[CH:18]4)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参与物

7

反应物 5

HCID 8028四氢呋喃HCID 11776三苯基膦HCID 75555偶氮二甲酸二异丙酯HCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneHCID 178521548HCID 178521548，化合物

产物 1

HCID 178421572HCID 178421572，化合物收率 97%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

The mixture of trans-4-phenyl-cyclohexanol (86.9 mg, 0.000493 mol), (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (Example 4, 100.0 mg, 0.0004111 mol) and triphenylphosphine (129 mg, 0.000493 mol) in tetrahydrofuran (4 mL, 0.05 mol) was heated to reflux, and diisopropyl azodicarboxylate (0.0971 mL, 0.000493 mol) was added dropwise and was stirred and refluxed for 3 hours. TLC monitoring showed the reaction to be complete. The mixture was taken up into DCM and subjected to chromatographic purification with EtOAc/hexane (10:90 to 80:20) to give (R)-4-(6-(trans-4-phenyl-cyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (160 mg, 97% yield). LCMS 402.28 ([M+1]+, 100%).

后处理

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturerefluxed for 3 hours
  4. customthe reaction
  5. customsubjected to chromatographic purification with EtOAc/hexane (10:90 to 80:20)

来源与证据

ORD记录
ord-d6897cf3cf8c41ef8f4932e64b8527af
来源数据集
uspto-grants-2013_10
专利号
US08546359B2

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