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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 229802
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 229802
[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 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl ester (0.872 g, 3.19 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, 19 mg, 0.0227 mmol) was added and the reaction mixture was refluxed for 2 h. Additional bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (mg, 0.0108 mmol) was added and the reaction mixture 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 (0.72 g, 92%): 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. temperaturethe reaction mixture was refluxed for an additional 1.5 hours
  4. concentrationwas concentrated in vacuo by rotary evaporation
  5. customwas chromatographed (silica gel, 5% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d000d78496f54fe3a788c55061ebd08d
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07563784B2

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