四氢呋喃 → HCID 178445732，化合物

HRID 1036382

反应方程式

HRID 1036382 反应方程式
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([OH:11])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].O[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C@:23]1([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]1)[CH:17]=[CH:16]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>>[CH2:1]([C@@H:5]1[CH2:6][CH2:7][C@H:8]([O:11][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([C@:23]2([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]2)[CH:17]=[CH:16]3)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

参与物

6

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 178445814HCID 178445814，化合物

产物 1

HCID 178445732HCID 178445732，化合物收率 88.3%

实验过程

A mixture of trans-4-butyl-cyclohexanol (441 mg, 2.82 mmol), ((R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (572.5 mg, 2.353 mmol) and triphenylphosphine (741 mg, 2.82 mmol) in tetrahydrofuran (20 mL, 0.3 mol) was heated to reflux, and diisopropyl azodicarboxylate (0.556 mL, 2.82 mmol) was added dropwise. The reaction was stirred and refluxed for 3 hours. TLC and LCMS monitoring showed the reaction to be incomplete. The mixture was concentrated and taken up into dichloromethane and subjected to chromatography purification with EtOAc/hexane (10:90 to 80:20) to give product (0.793 g, 88% yield). LCMS 2.35 min (382.93, [M+1], 100%).

后处理

  1. temperatureto reflux
  2. temperaturerefluxed for 3 hours
  3. customthe reaction
  4. concentrationThe mixture was concentrated
  5. customsubjected to chromatography purification with EtOAc/hexane (10:90 to 80:20)

来源与证据

ORD记录
ord-621d9c0bc0414cdfaf6ba2f5d04cb683
来源数据集
uspto-grants-2013_10
专利号
US08546359B2

关联笔记

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