Ammonium Chloride → HCID 178486029, Verbindung

HRID 2057256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2057256
[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([CH:15]=[C:16](Br)Br)[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.Br[CH2:26][CH2:27][CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1.[NH4+].[Cl-]>C1COCC1.CN1C(=O)N(C)CCC1>[C:1]([O:5][C:6](=[O:19])[N:7]([CH3:8])[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:26][CH2:27][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 178418339ButyllithiumHCID 178486027HCID 178486027, Verbindung

Produkt 1

HCID 178486029HCID 178486029, VerbindungAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Versuchsvorschrift

A solution of 3.97 g (10 mmol) of trans-[4-(2,2-Dibromo-vinyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 160 ml THF was treated at −78° C. with 13.13 ml (21 mmol) of BuLi (ca 1.6 M in hexane) and stirred for 2 h. 11 ml DMPU were added and 10 min later 4.60 g (20 mmol) of 1-bromo-3-tetrahydropyranyloxypropane in 15 ml THF were added over a period of 20 min. The reaction mixture was warmed up to RT for 16 h, cooled, poured into cooled aqueous saturated NH4Cl and extracted (Et2O 3×). The organic phase was washed with aqueous 10% NaCl, water, dried over Na2SO4, evaporated and purified by flash silica gel column (Hexane/EtOAc 98:2 to 90:10) to yield 1.61 g (42%) of trans-Methyl-{4-[5-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-cyclohexyl}-carbamic acid tert-butyl ester, MS: 378 (M−H).

Aufarbeitung

  1. additionwere added over a period of 20 min
  2. temperaturecooled
  3. additionpoured
  4. extractionextracted (Et2O 3×)
  5. washThe organic phase was washed with aqueous 10% NaCl, water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. custompurified by flash silica gel column (Hexane/EtOAc 98:2 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-15b1a2540a5e49e8806bf0dcb53b1efd
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335687B2

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