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Cyclohexylisopropylamine → HCID 20461593, Verbindung

HRID 1388287
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1388287
[CH:1](NC1CCCCC1)(C)C.C([Li])CCC.[CH2:16]([CH:19]1[N:22]([C:23]([C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:44])=[P:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21](=[O:53])[CH2:20]1)[CH:17]=[CH2:18]>O1CCCC1.CCCCCC>[CH2:16]([CH:19]1[N:22]([C:23]([C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:44])=[P:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:21](=[O:53])[CH:20]1[CH3:1])[CH:17]=[CH2:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62386CyclohexylisopropylamineHCID 127969694-Allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-oneHCID 178418339Butyllithium

Produkt 1

HCID 20461593HCID 20461593, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8058
Hexane
Lösungsmittel

Versuchsvorschrift

A solution of N-isopropylcyclohexylamine (0.30 g) in dry tetrahydrofuran (5 ml) was stirred under argon and cooled to -78°. This was treated with a 2.5 M solution of n-butyl lithium in hexane (0.85 ml) and stirred for 10 minutes. A solution of 4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidine-2-one (9) (0.50 g) in tetrahydrofuran (5 ml) was added and after 5 minutes the anion was quenched by addition of methyl iodide (0.12 ml). After a period of 10 minutes the reaction vessel was transferred to an ice bath and a further 10 minutes later the reaction was neutralized by addition of acetic acid (0.16 ml). The solvent was then stripped off and the residue partitioned between ethyl acetate and brine. The ethyl acetate solution was separated, washed with brine and dried over sodium sulphate. The product was subjected to careful column chromatography on silica gel 60 eluting with cyclohexane/ethyl acetate mixtures grading from 1:1 to 3:7. This gave 4-allyl-3-methyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidine-2-one (38) (0.10 g, 19%); νmax (CHCl3) 3000, 1735 and 1610 cm.-1Running closely behind this was recovered starting phosphorane (9) (0.17 g. 33%).

Aufarbeitung

  1. temperaturecooled to -78°
  2. customwas quenched by addition of methyl iodide (0.12 ml)
  3. waitAfter a period of 10 minutes the reaction vessel was transferred to an ice bath and a further 10 minutes
  4. additionlater the reaction was neutralized by addition of acetic acid (0.16 ml)
  5. customthe residue partitioned between ethyl acetate and brine
  6. customThe ethyl acetate solution was separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulphate
  9. custom-1Running closely behind this was recovered

Quellen und Nachweise

ORD-Eintrag
ord-726f12acb8404876b528977577a8eb3b
Quelldatensatz
uspto-grants-1984_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04431587

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