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Diisopropylethylamine → 1-[1-(4-Chloro-phenyl)-cyclobutanecarbonyl]-azetidine-3-carboxylic acid methyl ester

HRID 1160349
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1160349
Cl.[CH3:2][O:3][C:4]([CH:6]1[CH2:9][NH:8][CH2:7]1)=[O:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([C:21](O)=[O:22])[CH2:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:2][O:3][C:4]([CH:6]1[CH2:9][N:8]([C:21]([C:17]2([C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][CH:15]=3)[CH2:18][CH2:19][CH2:20]2)=[O:22])[CH2:7]1)=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acidHCID 2733179PyBroPHCID 21100040Methyl azetidine-3-carboxylate hydrochloride

Produkt 1

HCID 587375011-[1-(4-Chloro-phenyl)-cyclobutanecarbonyl]-azetidine-3-carboxylic acid methyl esterAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of azetidine-3-carboxylic acid methyl ester hydrochloride (762 mg, 4.60 mmoles) and 1-(4-chloro-phenyl)-cyclobutane carboxylic acid (2.09 g, 9.90 mmoles) in anhydrous DCM (20 mL) was added di-isopropyl ethyl amine (4.6 mL, 26.4 mmoles) dropwise. After completion of addition solid PyBroP (4.63 g, 9.94 mmoles) was added to the stirring reaction mixture. The reaction mixture continued stirring at RT for 10 h and was quenched with water. The aqueous layer was extracted with EtOAc (3×20 mL). Combined organic layers were dried over Na2SO4 and concentrated to yield an oil. This crude material was purified using silica gel chromatography (9:1 hexanes:EtOAc-1:1 hexane:EtOAc) to yield the desired amide (1.0 g, 65%). 1H NMR (300 MHz, CDCl3): δ 7.38-7.29 (m, 4H), 4.16 (m, 2H), 3.88 (m, 1H), 3.72 (s, 3H), 3.31-1.63 (m, 8H). LRMS: M+309.

Aufarbeitung

  1. additionwas added to the stirring reaction mixture
  2. customwas quenched with water
  3. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  4. dry with materialCombined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customto yield an oil
  7. customThis crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-f1d4ba7816bf4696a9e94429f41d858e
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07816375B2

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