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

HRID 225787노트

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HRID 225787 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f85b67926cca4a24859b49b9ccef073b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557126B2

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