Reaktion #40651

Reaktionsgleichung

4-isobutoxybenzyl bromide

NaH

84AF84-19

1-(4-Fluorobenzyl)-3-oxo-1,2,8-triaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester

→

desired compound

Ausbeute 50.6%

1-(4-Fluorobenzyl)-2-(4-isobutoxybenzyl)-3-oxo-1,2,8-triaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester

Ausbeute 50.6%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter 1 h stirring at rt the mixture
2. 2
   Sonstigewas partitioned between ethyl acetate and water
3. 3
   TrocknenThe organic layer was dried over sodium sulphate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigePurification of the residue by column chromatography on silica gel
7. 7
   Wascheneluting with a stepwise gradient of 3-6% methanol in dichloromethane

Vorschrift

NaH (24 mg, 0.50 mmol) was added slowly to a solution of 84AF84-19 (0.149 g, 0.41 mmol) in dry DMF (5 mL) and the mixture stirred at rt for 30 min. A solution of 4-isobutoxybenzyl bromide 69NLS69 (117 mg, 0.48 mmol) in dry DMF (1 mL) was added dropwise to the mixture. After 1 h stirring at rt the mixture was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with a stepwise gradient of 3-6% methanol in dichloromethane, followed by preparative reversed phase HPLC (C18) afforded the desired compound (109 mg, 50%).

Quelle