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Sodium Bicarbonate → 4-(methoxycarbonyl)phenyl (3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine-1-carboxylate

HRID 732650
ノート
印刷プレビュー

反応式

HRID 732650 の反応式
[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[CH2:13][NH:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].Cl[C:26]([O:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1)=[O:27]>O1CCCC1.O>[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[CH2:13][N:12]([C:26]([O:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=2)=[O:27])[CH2:11]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 854163Methyl 4-[(chlorocarbonyl)oxy]benzoate2 回HCID 68913849(3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine

生成物 1

HCID 866285334-(methoxycarbonyl)phenyl (3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 21881883
Oxolane--water (1/1)
溶媒

実験手順

A 350 mg portion of (3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine and 470 mg of sodium bicarbonate were suspended in 20 ml of a tetrahydrofuran-water (3:1) mixed solvent, and 320 mg of methyl 4-[(chlorocarbonyl)oxy]benzoate (mfd. by Fluka) was added in one portion thereto at room temperature. After 1Hour of stirring at room temperature, 80 mg of methyl 4-[(chlorocarbonyl)oxy]benzoate was further added thereto at room temperature. After 2 hours of further stirring, the reaction solution was concentrated under a reduced pressure. The residue was separated by diluting it with water and diethyl ether, and then extracted with diethyl ether. The organic layer was washed with water and saturated brine in that order and dried with anhydrous sodium sulfate. This was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-ethyl acetate) to obtain 571 mg of 4-(methoxycarbonyl)phenyl (3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine-1-carboxylate as a colorless oily substance.

後処理

  1. additionwas added in one portion
  2. customat room temperature
  3. customat room temperature
  4. concentrationthe reaction solution was concentrated under a reduced pressure
  5. customThe residue was separated
  6. additionby diluting it with water and diethyl ether
  7. extractionextracted with diethyl ether
  8. washThe organic layer was washed with water and saturated brine in that order
  9. dry with materialdried with anhydrous sodium sulfate
  10. concentrationThis was concentrated under a reduced pressure
  11. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-ethyl acetate)

出典と根拠

ORDレコード
ord-c0472953b06e422fa038fcb1cf509e4a
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07585886B2

反応ノート

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