Sodium Thiosulfate → Iometopane

HRID 343995ノート

反応式

HRID 343995 の反応式
[C:1]([C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([Si](C)(C)C)=[CH:14][CH:13]=2)[CH2:10][C@H:9]2[N:22]([CH3:23])[C@@H:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2].[I:24]Cl.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)(Cl)Cl>[C:1]([C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([I:24])=[CH:14][CH:13]=2)[CH2:10][C@H:9]2[N:22]([CH3:23])[C@@H:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2]

参加物

6

反応物 4

HCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 516892Sodium BicarbonateHCID 697363762beta-Carbomethoxy-3beta-(4-trimethylsilylphenyl)tropane

生成物 1

HCID 108220Iometopane

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

50 mg of 2β-carbomethoxy-3β-(4-trimethylsilylphenyl)tropane was dissolved in 5 ml of CCl4 at ambient temperature. To this was added 40 mg of iodine monochloride after which the solution was stirred for 2 h, then poured into 20 mL of 10% sodium thiosulfate (Reaction 7). The two phase solution was shaken until the dark color disappeared, made basic with saturated sodium bicarbonate, and the organic layer separated. The aqueous layer was extracted three times with 10 mL portions of CHCl3 and the combined organic layers were then washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was dissolved in a small portion of ether and chromatographed using a flash SiO2 column (10"×1/2", ether/hexane 1/2) and the eluents concentrated to yield 53 mg of (91%) CIT. No isomerization of the ester moiety was detected by TLC or NMR.

後処理

  1. stirringThe two phase solution was shaken until the dark color
  2. customthe organic layer separated
  3. extractionThe aqueous layer was extracted three times with 10 mL portions of CHCl3
  4. washthe combined organic layers were then washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in a small portion of ether
  8. customchromatographed
  9. concentrationthe eluents concentrated
  10. customto yield 53 mg of (91%) CIT

出典と根拠

ORDレコード
ord-62daa06338ac48a684ef7eec66a10df3
出典データセット
uspto-grants-1999_01
特許番号
US05864038

反応ノート

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