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Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl ester → Benzyl 2-methyl-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate

HRID 229793
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 229793
[CH2:1]([O:8][C:9](=[O:20])[N:10]([CH2:17][CH:18]=C)[CH:11](C)[CH2:12][CH2:13][CH:14]=[CH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.C=CC1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru]Cl>[CH2:1]([O:8][C:9]([N:10]1[CH2:11][CH:12]=[CH:13][CH2:14][CH2:15][CH:17]1[CH3:18])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 11608774Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl ester

Produkt 1

HCID 11586812Benzyl 2-methyl-2,3,4,7-tetrahydro-1H-azepine-1-carboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 60145889Benzylidene-bis(triphenylphosphine)ruthenium dichlorideKatalysator2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl ester (1.036 g, 3.8 mmol) was dissolved in CH2Cl2 (10 ml) and a stream of argon gas was bubbled into the reaction mixture for 10 minutes. Then bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (Strem Chemicals, Grubbs' catalyst, 22 mg, 0.027 mmol) was added and the reaction mixture was refluxed for 2 h. Additional bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (11 mg, 0.014 mmol) was added and the reaction mixtrue was refluxed for an additional 1.5 hours. The reaction was cooled to RT under argon overnight, then was concentrated in vacuo by rotary evaporation, then was chromatographed (silica gel, 5% EtOAc/hexanes) to give the title compound (0.83 g, 89%): 1H NMR: 7.35-7.20 (m, 5H), 5.65 (1H, m), 5.13 (2H, AB), 4.45-4.05 (m, 2H), 3.56 (1H, d), 2.25-2.10 (m, 2H), 1.90-1.60 (m, 2H), 1.12 (3H, d); Liquid Chromatgraphy/Electrospray mass spec: M+H+=246.2.

Aufarbeitung

  1. customa stream of argon gas was bubbled into the reaction mixture for 10 minutes
  2. temperaturethe reaction mixture was refluxed for 2 h
  3. customthe reaction
  4. temperaturemixtrue was refluxed for an additional 1.5 hours
  5. concentrationwas concentrated in vacuo by rotary evaporation
  6. customwas chromatographed (silica gel, 5% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5e7ab8c414b14c0d97b8812e1b9454e0
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07563784B2

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