Reaktion #2000650

Reaktionsgleichung

tert-butyl 2-((R)-5-(5-cyanopyrazin-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate

tert-Butyl 2-((R)-5-(5-cyanopyrazin-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate

water

urea hydrogen peroxide

Sodium hydroxide

→

title compound

Ausbeute 53.3%

2-[(R)-5-(5-Carbamoyl-pyrazin-2-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester

Ausbeute 53.3%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeOnce a clear solution was obtained
2. 2
   Sonstigethe reaction was placed in an ice bath
3. 3
   Sonstigefitted with an addition funnel
4. 4
   TemperaturThe reaction was warmed to room temperature
5. 5
   workup.STIRRINGstirred overnight
6. 6
   FiltrationThe resulting white suspension was collected by vacuum filtration
7. 7
   WaschenThe solids were washed with 50 mL water
8. 8
   Sonstigeair-dried

Vorschrift

A round-bottomed flask was charged with water (100 mL) and urea hydrogen peroxide (495 mg, 5.11 mmol). Sodium hydroxide (119 mg, 2.98 mmol) was added and the reaction was stirred at room temperature. Once a clear solution was obtained, the reaction was placed in an ice bath and fitted with an addition funnel. A solution of tert-butyl 2-((R)-5-(5-cyanopyrazin-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate (10-1a, 379 mg, 0.85 mmol) in 25 mL EtOH was added dropwise over a period of 30 minutes via the funnel. The reaction was warmed to room temperature and stirred overnight. The resulting white suspension was collected by vacuum filtration. The solids were washed with 50 mL water and air-dried to give 210 mg (53%) of the title compound as an off-white powder. MS (ES+) 464.4 (M+H)+. 1H NMR (DMSO-d6) δ 1.38 (s, 9H), 1.54-1.61 (m, 4H), 1.89 (d, 1H), 2.08 (s, 1H), 2.76-2.80 (m, 2H), 2.99 (d, 3H), 3.11 (d, 2H), 3.19-3.22 (m, 3H), 3.90 (d, 1H), 7.45 (d, 1H), 7.83 (br s, 1H), 8.01 (d, 1H), 8.08 (s, 1H), 8.23 (s, 1H), 9.20 (d, 1H), 9.24 (d, 1H).

Quelle