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Dicyclohexylamine → (r)-2-Bromoisovaleric acid dicyclohexylamine salt

HRID 1452816
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1452816
[Br:1][C@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[CH:9]1([NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>CCCCCC>[CH:16]1([NH:15][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1.[Br:1][C@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 7582DicyclohexylamineHCID 156968alpha-Bromoisovaleric acid, (R)-

Produkt 1

HCID 86600188(r)-2-Bromoisovaleric acid dicyclohexylamine saltAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To 325.2 g of a hexane solution of (R)-2-bromoisovaleric acid obtained in Example 4 (containing 75.0 g of (R)-2-bromoisovaleric acid), 530.9 g of hexane and 269.7 g of2-propanol were further added. Seed crystals were added when about ⅔ for 72.5 g of dicyclohexylamine was added continuously for 1.0 hour under a nitrogen atmosphere at 5° C. to crystallize. Further, after continuously adding the remaining about ⅓ for dicyclohexylamine at 5° C. for 0.5 hours, they were stirred at 5° C. for 1 hour. The obtained crystals were filtered under a reduced pressure and then the crystals were washed for 3 times with 150 ml of hexane. The obtained wet crystals were dried under a reduced pressure to obtain 126.45 g of a (R)-2-bromoisovaleric acid dicyclohexylamine salt (optical purity 98.0% ee, crystallization yield 87%, apparent purity 98.9%, impurity content 2-hydroxy isovaleric acid: not detected, bromine content: 0.64%).

Aufarbeitung

  1. additionwas added continuously for 1.0 hour under a nitrogen atmosphere at 5° C.
  2. customto crystallize
  3. additionFurther, after continuously adding the remaining about ⅓ for dicyclohexylamine at 5° C. for 0.5 hours
  4. filtrationThe obtained crystals were filtered under a reduced pressure
  5. washthe crystals were washed for 3 times with 150 ml of hexane
  6. customThe obtained wet crystals were dried under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8aabeecc75714453ac8bef67fa28756f
Quelldatensatz
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07473803B2

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