Propargyl bromide → 2-(4-Prop-2-ynyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 12924

Reaktionsgleichung

Reaktionsgleichung von HRID 12924
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[C:29]#[CH:30]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:30][C:29]#[CH:28])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 59752861(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 866196562-(4-Prop-2-ynyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of the product from step 2 (2.0 g, 6.82 mmol) in anhydrous DMF (50 mL) was added dry K2CO3 (4.6 g, 33 mmol) and allowed to stir for 15 min. Propargyl bromide (1.214 g, 10.20 mmol) in anhydrous DMF (10 mL) was added and the reaction mixture stirred at 50° C. for 6 h, then at rt for 48 h. The reaction mixture was concentrated, taken up in EtOAc, washed with water, dried over anhydrous MgSO4 and the solvent removed in vacuo. The product was purified by silica gel flash chromatography using EtOAc/hexane to obtain the title compound (2.0 g, 88%).

Aufarbeitung

  1. stirringthe reaction mixture stirred at 50° C. for 6 h
  2. waitat rt for 48 h
  3. concentrationThe reaction mixture was concentrated
  4. washwashed with water
  5. dry with materialdried over anhydrous MgSO4
  6. customthe solvent removed in vacuo
  7. customThe product was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c118b8ac54d14d2ab9d48661c465d8e7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728032B2

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