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Potassium Carbonate → Tert-butyl(trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropylcarbamate

HRID 1746094
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1746094
[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br>CN(C=O)C>[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][O:17][C:14]1[CH:15]=[CH:16][C:11]([C@@H:9]2[CH2:10][C@H:8]2[NH:7][C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:12][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 86672576tert-Butyl N-[(1R,2S)-rel-2-(4-hydroxyphenyl)cyclopropyl]carbamate2×

Produkt 1

HCID 86680873Tert-butyl(trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropylcarbamateAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of tert-butyl-(trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate (Intermediate N, 5 g, 20.0 mmol), K2CO3 (6.8 g, 50.0 mmol) in dry DMF (10 vols) was added 3-Bromo benzyl bromide (5 g, 20.0 mmol) and stirred at RT for 16 h. After completion, the reaction mixture was poured into ice water (150 mL) and extracted with EtOAc (2×75 mL). The combined extracts were washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography to give (tert-butyl(trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropylcarbamate (5.2 g, 62%) as a white solid. The crude was carried to next step without further purification.

Aufarbeitung

  1. extractionextracted with EtOAc (2×75 mL)
  2. washThe combined extracts were washed with water (100 mL), brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8e6c61a8e85c4ffdbc05061fc600898c
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09149447B2

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