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Triethylamine → methyl 2-benzyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

HRID 1169317
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1169317
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]2[CH2:13][CH2:14][CH2:15][CH:16]([C:19]([O:21][CH3:22])=[O:20])[C:17](=O)[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(N(CC)CC)C.CS(Cl)(=O)=O.C1CCN2C(=NCCC2)CC1>ClCCl.CO.O>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]2[CH2:13][CH2:14][CH2:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 4311764Sodium borohydrideHCID 22990024methyl 3-benzyloxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate

Produkt 1

HCID 22989957
methyl 2-benzyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate
Ausbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To methyl 3-benzyloxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylate (2.81 g, 8.66 mmol) dissolved in a mixed solvent of dichloromethane (40 ml) and methanol (10 ml) was added at −40° C. (inner temperature) sodium borohydride (500 mg, 13.2 mmol), and the resulting mixture was stirred at −15° C. to −10° C. for 2 hours. The reaction mixture was cooled to −40° C., was mixed with water (20 ml) and extracted with dichloromethane (40 ml, 10 ml×2). The combined organic layers were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure. To the residue dissolved in THF (30 ml) were added at 0° C. triethylamine (6.04 ml, 43.3 mmol) and methanesulfonyl chloride (1.10 ml, 13.0 mmol), and the resulting mixture was stirred at room temperature for 20 hours. In order to complete the reaction, DBU (3.89 ml, 26.0 mmol) was added, and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, was mixed with water and was extracted with ethyl acetate (30 ml×3). The combined organic layers were washed with 1 N hydrochloric acid (5 ml×3), were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 60 g, ethyl acetate/hexane=1/30 →1/9). The objective fractions were concentrated under reduced pressure to obtain methyl 2-benzyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (2.32 g, 7.52 mmol, 87%).

Aufarbeitung

  1. extractionextracted with dichloromethane (40 ml, 10 ml×2)
  2. dry with materialThe combined organic layers were dried with anhydrous magnesium sulfate
  3. concentrationwere then concentrated under reduced pressure
  4. dissolutionTo the residue dissolved in THF (30 ml)
  5. stirringthe resulting mixture was stirred at room temperature for 20 hours
  6. additionwas added
  7. stirringthe resulting mixture was stirred at room temperature for 24 hours
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. additionwas mixed with water
  10. extractionwas extracted with ethyl acetate (30 ml×3)
  11. washThe combined organic layers were washed with 1 N hydrochloric acid (5 ml×3)
  12. dry with materialwere dried with anhydrous magnesium sulfate
  13. concentrationwere then concentrated under reduced pressure
  14. concentrationThe objective fractions were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4ae289e695c7460b8c4b4479f18ef802
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06627651B1

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