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Dichloromethane → 1,2,3,3a,8,8a-Hexahydro-alpha-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, phenylethyl ester

HRID 1681636
ノート
印刷プレビュー

反応式

HRID 1681636 の反応式
[O:1]=[C:2]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]1[N:18]([CH3:21])[CH2:19][CH2:20][C:11]21[CH3:22])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH4+].[Cl-].C(Cl)Cl>C1(CCO)C=CC=CC=1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[O:1]=[C:2]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]1[N:18]([CH3:21])[CH2:19][CH2:20][C:11]21[CH3:22])[C:3]([O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:14]=[CH:15][CH:16]=1)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 867464181,2,3,3a,8,8a-Hexahydro-alpha-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, ethyl ester

生成物 1

HCID 867464191,2,3,3a,8,8a-Hexahydro-alpha-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, phenylethyl ester収率 151.4%

試薬・触媒・溶媒 2

HCID 76524
Titanium tetraethoxide
触媒
HCID 60542-Phenylethanol溶媒

実験手順

To a chilled (0° C.) solution of 1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, ethyl ester (0.76 g) in anhydrous phenylethyl alcohol (18.1 ml) was added titanium (IV) ethoxide (0.22 ml) via syringe under a nitrogen atmosphere. The solution was warmed to room temperature and heated to just under reflux for 3 hours. The solution was then cooled to 0° C. and saturated NH4Cl solution was added slowly until a precipitate formed. Methylene chloride (200 ml) was then added and the mixture extracted twice with 100 ml portions of saturated aqueous NH4Cl solution, twice with 100 ml of saturated aqueous NaHCO3 and once with 100 ml of brine. The organic extracts were dried (Na2SO4), filtered, and the solvent removed on the rotary evaporator. The phenylethyl alcohol was then removed by distillation under high vacuum. The resulting residue was purified using preparative HPLC (silica gel, 4% methanol in ethyl acetate as the loading solvent and eluent). The appropriate fractions were combined, and the solvent removed to yield 0.72 g of 1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, phenylethyl ester, as an oil.

後処理

  1. temperatureheated to just
  2. temperatureunder reflux for 3 hours
  3. temperatureThe solution was then cooled to 0° C.
  4. customformed
  5. extractionthe mixture extracted twice with 100 ml portions of saturated aqueous NH4Cl solution, twice with 100 ml of saturated aqueous NaHCO3 and once with 100 ml of brine
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent removed on the rotary evaporator
  9. customThe phenylethyl alcohol was then removed by distillation under high vacuum
  10. customThe resulting residue was purified
  11. customthe solvent removed

出典と根拠

ORDレコード
ord-5c91810484764d6282f1228a2afa6f09
出典データセット
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05173497

反応ノート

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