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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
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HRID 1681636 반응식
[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]
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6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 76524
Titanium tetraethoxide
촉매
HCID 60542-Phenylethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5c91810484764d6282f1228a2afa6f09
출처 데이터셋
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05173497

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