Diisopropylethylamine → {3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl}carbamic acid tert-butyl ester

HRID 1182099

Reaktionsgleichung

Reaktionsgleichung von HRID 1182099
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][CH:7]2[CH2:10][NH:9][CH2:8]2)=[CH:4][CH:3]=1.[C:13]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH2:21][CH2:22]Br)([CH3:16])([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:13]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH2:21][CH2:22][N:9]1[CH2:8][CH:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:12][CH:11]=2)[CH2:10]1)([CH3:16])([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 167807403-(4-Chlorobenzyl)azetidine

Produkt 1

HCID 69411053{3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl}carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-(4-chloro-benzyl)-azetidine (1.0 g, 5.50 mmol), (3-bromo-propyl)-carbamic acid tert-butyl ester (1.31 g, 5.50 mmol) and diisopropylethylamine (1.91 ml, 11.0 mmol) in dry dimethylformamide (20 ml) is stirred at ambient temperature for 18 hours. The reaction mixture is partitioned between ethylacetate and water. The organic phase is washed with water and brine, dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography using 5% methanol in dichloromethane as eluent to afford {3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl]-carbamic acid tert-butyl ester. [M+H] 339.15

Aufarbeitung

  1. customThe reaction mixture is partitioned between ethylacetate and water
  2. washThe organic phase is washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ebaec3e3ec054545bb38a819cf009fa8
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288537B2

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