Diethylene glycol vinyl ether → tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

HRID 522220

Reaktionsgleichung

Reaktionsgleichung von HRID 522220
[CH2:1]([N:5]([CH2:13][CH2:14][C:15]([B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]1)=[CH2:16])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2]C=C.C(OCCOCCO)=C>CC1CCCCC1.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1>[CH3:23][C:20]1([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18][B:17]([C:15]2[CH2:14][CH2:13][N:5]([C:6]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12])[CH2:1][CH2:2][CH:16]=2)[O:21]1

Komponenten

5

Edukt 2

HCID 13581Diethylene glycol vinyl etherHCID 131735521Tert-butyl but-3-en-1-yl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)carbamate

Produkt 1

HCID 68054971tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichlorideKatalysatorHCID 7962MethylcyclohexaneLösungsmittel

Versuchsvorschrift

A solution of Example 87B (7.28 g, 20.72 mmol) in methyl cyclohexane (1.5 L) was degassed with nitrogen and (1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium (250 mg, 0.294 mmol) was added. The mixture was stirred at room temperature overnight and diethyleneglycol vinyl ether (0.16 mL) was added to inactivate any remaining active catalyst. The mixture was stirred for 30 minutes, concentrated and purified by flash chromatography on silica using an Analogix system (0-10% ethyl acetate/heptane) to provide the title compound. MS (ESI+) m/z 346 (M+Na)+.

Aufarbeitung

  1. additionwas added
  2. stirringThe mixture was stirred for 30 minutes
  3. concentrationconcentrated
  4. custompurified by flash chromatography on silica using an Analogix system (0-10% ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-4eb3b16da39049bb9d025d1ac48bcd79
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328112B2

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