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

HRID 225787ノート

反応式

HRID 225787 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 MeOH (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 hours. 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 MeOH (20 mL). The filtrate was collected and most of the MeOH was removed in vacuo. The residue was mixed with IPAc (100 mL) and 10% aqueous sodium carbonate (50 mL). The resulting layers were separated and the aqueous layer was extracted with IPAc (50 mL). The organic layers were combined and dried over sodium sulfate (20 g). The sodium sulfate was filtered off and washed with IPAc (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 MeOH (20 mL)
  4. customThe filtrate was collected and most of the MeOH
  5. customwas removed in vacuo
  6. additionThe residue was mixed with IPAc (100 mL) and 10% aqueous sodium carbonate (50 mL)
  7. customThe resulting layers were separated
  8. extractionthe aqueous layer was extracted with IPAc (50 mL)
  9. dry with materialdried over sodium sulfate (20 g)
  10. filtrationThe sodium sulfate was filtered off
  11. washwashed with IPAc (20 mL)
  12. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-f85b67926cca4a24859b49b9ccef073b
出典データセット
uspto-grants-2009_07
特許番号
US07557126B2

反応ノート

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