Octyl isocyanate → 3-[1-Phenylmethyl-2-pyrrolidinyl]phenyl octylcarbamate

HRID 1654045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654045
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([N:28]=[C:29]=[O:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>O1CCCC1>[CH2:20]([NH:28][C:29](=[O:30])[O:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:9]2[CH2:10][CH2:11][CH2:12][N:8]2[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

4

Edukt 2

HCID 76616Octyl isocyanateHCID 233612863-(1-Phenylmethyl-2-pyrrolidinyl)phenol

Produkt 1

HCID 152913763-[1-Phenylmethyl-2-pyrrolidinyl]phenyl octylcarbamateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(1-phenylmethyl-2-pyrrolidinyl)phenol (0.06 g) in dry tetrahydrofuran (30 ml) was added octyl isocyanate (0.44 ml) at ambient temperature, under nitrogen. The reaction mixture was stirred for 17 hrs and filtered through a pad of celite. The filter cake was washed with ethyl acetate and the combined filtrates were concentrated. The residue was purified by flash column chromatography (silica gel, dichloromethane). The appropriate fractions were collected and concentrated to give 0.50 g (52%) of product. The analytical sample was prepared by flushing the product through alumina with ether.

Aufarbeitung

  1. filtrationfiltered through a pad of celite
  2. washThe filter cake was washed with ethyl acetate
  3. concentrationthe combined filtrates were concentrated
  4. customThe residue was purified by flash column chromatography (silica gel, dichloromethane)
  5. customThe appropriate fractions were collected
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-adab800f492c47fd97917617982fd9da
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05405845

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