Water → (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)acetonitrile

HRID 350820ノート

反応式

HRID 350820 の反応式
Cl.C([N:9]1[CH2:13][CH2:12][C@@H:11]([C:14]([C:27]#[N:28])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+].O>CO.[Pd]>[C:27]([C:14]([C@@H:11]1[CH2:12][CH2:13][NH:9][CH2:10]1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[N:28]

参加物

6

反応物 3

HCID 962WaterHCID 2723923Ammonium formateHCID 66855790((S)-1-benzylpyrrolidin-3-yl)diphenylacetonitrile hydrochloride

生成物 1

HCID 22842833(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)acetonitrile収率 99.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of (S)-1-benzyl-3-(1-cyano-1,1-diphenylmethyl)pyrrolidine hydrochloride (8.55 g, 21.98 mmol) in methanol (44 mL) was added palladium on carbon (1.71 g) and ammonium formate (6.93 g, 109.9 mmol). The reaction mixture was heated to 50° C. with stirring for 3 h. The reaction was cooled to ambient temperature and water (20 mL) was added. The resulting mixture was filtered through a pad of Celite, washing with methanol (20 mL). The filtrate was collected and most of the methanol was removed in vacuo. The residue was mixed with isopropyl acetate (100 mL) and 10% aqueous sodium carbonate (50 mL). The resulting layers were separated and the aqueous layer was extracted with isopropyl acetate (50 mL). The organic layers were combined and dried over sodium sulfate (20 g). The sodium sulfate was filtered off and washed with isopropyl acetate (20 mL). The solvent was removed in vacuo to afford 5.75 g of the title intermediate as a light yellow oil (99.7% yield, 71% purity by HPLC).

後処理

  1. temperatureThe reaction was cooled to ambient temperature
  2. filtrationThe resulting mixture was filtered through a pad of Celite
  3. washwashing with methanol (20 mL)
  4. customThe filtrate was collected and most of the methanol
  5. customwas removed in vacuo
  6. additionThe residue was mixed with isopropyl acetate (100 mL) and 10% aqueous sodium carbonate (50 mL)
  7. customThe resulting layers were separated
  8. extractionthe aqueous layer was extracted with isopropyl acetate (50 mL)
  9. dry with materialdried over sodium sulfate (20 g)
  10. filtrationThe sodium sulfate was filtered off
  11. washwashed with isopropyl acetate (20 mL)
  12. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-6d381008074a4e9b9db5666877591f45
出典データセット
uspto-grants-2007_02
特許番号
US07183292B2

反応ノート

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