海萝胶 → 2-[(5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren-7-yl)-oxymethl]imidazoline

HRID 364013

反应方程式

HRID 364013 反应方程式
[Na].[Cl:2][C:3]1[C:15]([Cl:16])=[C:14]([O:17][CH2:18][C:19]#[N:20])[CH:13]=[C:12]2[C:4]=1[C:5]1[C:10]([CH2:21][CH2:22][CH3:23])([CH2:11]2)[CH2:9][CH2:8][C:7](=[O:24])[CH:6]=1.Cl.Cl.[CH2:27](N)[CH2:28][NH2:29].Cl>CO>[Cl:2][C:3]1[C:15]([Cl:16])=[C:14]([O:17][CH2:18][C:19]2[NH:29][CH2:28][CH2:27][N:20]=2)[CH:13]=[C:12]2[C:4]=1[C:5]1[C:10]([CH2:21][CH2:22][CH3:23])([CH2:11]2)[CH2:9][CH2:8][C:7](=[O:24])[CH:6]=1

参与物

6

反应物 4

HCID 313海萝胶HCID 9521乙二胺二盐酸盐HCID 5360545钠HCID 13686916[(5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren-7-yl)oxy]acetonitrile

产物 1

HCID 136869202-[(5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren-7-yl)-oxymethl]imidazoline

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

实验过程

To a solution of sodium metal (20 mg) in methanol (30 ml) was added (+) [(5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propy-1H-fluoren-7-yl)oxy]-acetonitrile (1.05 g, 3.0 mMole). The reaction mixture was stirred for 11/4 hours in a nitrogen atmosphere then treated with ethylenediamine dihydrochloride (410 mg, 3.1 mMole) and stirring was continued for 2 hours. Ethanolic hydrogen chloride was added until the reaction mixture was just acidic. After 1/2 hour, the methanol was distilled at reduced pressure, the residue dissolved in water, treated with 10N sodium hydroxide (1 ml), extracted with ether containing 5% tetrahydrofuran, washed with water, brine, dried over potassium carbonate and evaporated to dryness to give the (+)-enantiomer of 2-[(5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren-7-yl)-oxymethl]imidazoline which melts at 152°-154° C.

后处理

  1. stirringstirring
  2. waitwas continued for 2 hours
  3. waitAfter 1/2 hour
  4. distillationthe methanol was distilled at reduced pressure
  5. dissolutionthe residue dissolved in water
  6. additiontreated with 10N sodium hydroxide (1 ml)
  7. extractionextracted with ether containing 5% tetrahydrofuran
  8. washwashed with water, brine
  9. dry with materialdried over potassium carbonate
  10. customevaporated to dryness

来源与证据

ORD记录
ord-f9d8d299455d44da8051962b5fcf0af0
来源数据集
uspto-grants-1986_08
专利号
US04604396

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