(8aR)-2-[1-(diphenylmethyl)azetidin-3-yl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one → (8aR)-2-azetidin-3-ylhexahydropyrrolo[1,2-a]pyrazin-6(2H)-one

HRID 2063303ノート

反応式

HRID 2063303 の反応式
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][N:15]4[C:18](=[O:21])[CH2:19][CH2:20][C@@H:14]4[CH2:13]3)[CH2:9]2)C=CC=CC=1>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:9][CH:10]([N:12]2[CH2:17][CH2:16][N:15]3[C:18](=[O:21])[CH2:19][CH2:20][C@@H:14]3[CH2:13]2)[CH2:11]1

参加物

4

反応物 1

HCID 16124368(8aR)-2-[1-(diphenylmethyl)azetidin-3-yl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one

生成物 1

HCID 16124369(8aR)-2-azetidin-3-ylhexahydropyrrolo[1,2-a]pyrazin-6(2H)-one収率 84%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 176Acetic Acid溶媒

実験手順

(8aR)-2-[1-(diphenylmethyl)azetidin-3-yl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one (0.23 g, 0.64 mmol) was dissolved in acetic acid (20 mL) and to the resultant solution was added palladium hydroxide on carbon (0.33 g). The mixture was stirred under hydrogen (5 bar) at RT for 48 h and then the catalyst was filtered off by means of Celite®. The solvent was removed by evaporation and the residue was dissolved in ethanol. The solution was filtered through a cation exchange column (Isolute SCX-2, 10 g). The column was washed with ethanol and then the product was eluted with ammonia-saturated methanol. The solvent was removed by evaporation and there was obtained 0.10 g (84%) of the title compound. 1H NMR (500 MHz, CDCl3): 1.5-1.6 (m, 2H), 1.8 (m, 1H), 2.1-2.2 (m, 1H), 2.3-2.4 (m, 2H), 2.7 (d, 1H), 2.8-2.9 (m, 2H), 3.2 (qn, 1H), 3.5-3.7 (m, 4H), 4.0 (dd, 1H).

後処理

  1. filtrationthe catalyst was filtered off by means of Celite®
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue was dissolved in ethanol
  4. filtrationThe solution was filtered through a cation exchange column (Isolute SCX-2, 10 g)
  5. washThe column was washed with ethanol
  6. washthe product was eluted with ammonia-saturated methanol
  7. customThe solvent was removed by evaporation

出典と根拠

ORDレコード
ord-1eab930ad2684cf283ab5e7771d28659
出典データセット
uspto-grants-2012_10
特許番号
US08288370B2

反応ノート

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