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Tris(1,1-dimethylethyl)phosphine → Benzyl 6-(3-(phenylsulfonyl)quinolin-8-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

HRID 2092190
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2092190
CC(C)([O-])C.[Na+].[C@@H:7]12[CH2:13][NH:12][C@@H:11]1[CH2:10][N:9]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:8]2.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.I[C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:47]=1[N:46]=[CH:45][C:44]([S:48]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=[O:50])=[O:49])=[CH:43]2>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:51]1([S:48]([C:44]2[CH:45]=[N:46][C:47]3[C:42]([CH:43]=2)=[CH:41][CH:40]=[CH:39][C:38]=3[N:12]2[CH2:13][CH:7]3[CH:11]2[CH2:10][N:9]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:8]3)(=[O:50])=[O:49])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 114067748-Iodo-3-(phenylsulfonyl)quinolineHCID 23635906benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylateHCID 23676156Sodium t-butoxide

Produkt 1

HCID 25196270Benzyl 6-(3-(phenylsulfonyl)quinolin-8-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of sodium t-butoxide (49 mg, 0.51 mmol) and (1S,5S)-benzyl 3,6-diazabicyclo[3.2.0]heptane-3-carboxylate (98 mg, 0.24 mmol) in toluene (3 mL) was stirred under nitrogen. To this was added tri-t-butylphosphine (25 mg, 0.05 mmol), palladium (II) acetate (6.9 mg, 0.03 mmol) and 8-iodo-3-(phenylsulfonyl)quinoline (80 mg, 0.202 mmol). The mixture was then heated at 60° C. for 2 h before partitioning between CH2Cl2 and water. The mixture was filtered through Celite and the organic phase was separated. The water phase was extracted twice with CH2Cl2 and the combined extracts dried (Na2SO4), filtered and concentrated in vacuo to provide the crude material, which was purified by flash chromatography to give the title compound.

Aufarbeitung

  1. custombefore partitioning between CH2Cl2 and water
  2. filtrationThe mixture was filtered through Celite
  3. customthe organic phase was separated
  4. extractionThe water phase was extracted twice with CH2Cl2
  5. dry with materialthe combined extracts dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide the crude material, which
  9. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9c7fb832eebb45c1a828443bceb61da8
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08440694B2

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