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Pyrrolidine → (S)-2'-(neopentyloxy)-7'-(pyrolidin-1-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335763
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 335763
Br[C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:9][CH:10]=3)[C@:5]3([CH2:25][O:24][C:23]([NH2:26])=[N:22]3)[C:4]=2[CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2[C:41]([N:46]([CH3:48])C)=[CH:42][CH:43]=CC=2)CCCCC1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.N1CCCC1>[Cl-].[NH4+].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:17]([O:16][C:8]1[CH:9]=[CH:10][C:11]2[O:12][C:13]3[C:4](=[CH:3][C:2]([N:46]4[CH2:41][CH2:42][CH2:43][CH2:48]4)=[CH:15][CH:14]=3)[C@@:5]3([CH2:25][O:24][C:23]([NH2:26])=[N:22]3)[C:6]=2[CH:7]=1)[C:18]([CH3:21])([CH3:20])[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 31268Pyrrolidine2×HCID 2733832Lithium hexamethyldisilazane2×HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl2×HCID 58466128(R)-2'-bromo-7'-(neopentyloxy)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Produkt 1

HCID 58466222(S)-2'-(neopentyloxy)-7'-(pyrolidin-1-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator2×HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A vial was charged with (R)-2′-bromo-7′-(neopentyloxy)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (0.100 g, 0.240 mmol), 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (1.132 mg, 2.88 μmol), Pd2(dba)3 (1.097 mg, 1.198 μmol), LiHMDS (1.0 M in THF) (0.959 mL, 0.959 mmol), and pyrrolidine (0.059 mL, 0.719 mmol). The vial was sealed and heated to 100° C. overnight. Additional Pd2(dba)3 (1.097 mg, 1.198 μmol), 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (1.132 mg, 2.88 μmol), LiHMDS (1.0 M in THF) (0.480 mL, 0.480 mmol) and pyrrolidine (0.059 mL, 0.719 mmol) were added and the reaction was at 100° C. for 2 hours. The reaction mixture was diluted with a saturated aqueous ammonium chloride solution (10 mL) and extracted three times with DCM. The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The material was purified via Gilson HPLC (20-90% MeCN:H2O). The product fractions were partitioned between DCM and saturated sodium bicarbonate solution. The aqueous layer was extracted with DCM, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford (S)-2′-(neopentyloxy)-7′-(pyrolidin-1-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as a white solid.

Aufarbeitung

  1. customThe vial was sealed
  2. extractionextracted three times with DCM
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe material was purified via Gilson HPLC (20-90% MeCN:H2O)
  7. customThe product fractions were partitioned between DCM and saturated sodium bicarbonate solution
  8. extractionThe aqueous layer was extracted with DCM
  9. dry with materialthe combined organic layers were dried with sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-695a41818d9b4b41ad78a54aaa682cef
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883782B2

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