Dimethyl Sulfoxide → tert-butyl {[(3R,4S)-1-(4-cyanophenyl)-4-phenylpyrrolidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate

HRID 732640노트

반응식

HRID 732640 반응식
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[C:16]1([C@H:26]([N:28]([CH2:36][C@@H:37]2[C@@H:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:40][NH:39][CH2:38]2)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.CS(C)=O>C(OCC)(=O)C>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:39]2[CH2:40][C@H:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:37]([CH2:36][N:28]([C@@H:26]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)[CH3:27])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:38]2)=[CH:9][CH:10]=1)#[N:13]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 86628525tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate

생성물 1

HCID 86628530tert-butyl {[(3R,4S)-1-(4-cyanophenyl)-4-phenylpyrrolidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate수율 58.6%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

A 650 mg portion of potassium carbonate and 339 mg of 4-fluorobenzonitrile were added to a mixture of 1.0 g of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate and 10 ml of DMSO and stirred overnight at 110° C. After cooling down to room temperature, the reaction solution was mixed with ethyl acetate, washed with water and saturated brine in that order and dried with anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (hexane-ethyl acetate) to obtain 723 mg of tert-butyl {[(3R,4S)-1-(4-cyanophenyl)-4-phenylpyrrolidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate as a colorless amorphous substance. EP: 532.

후처리

  1. temperatureAfter cooling down to room temperature
  2. washwashed with water and saturated brine in that order
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was evaporated under a reduced pressure
  5. customthe thus obtained residue was purified by a silica gel column chromatography (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-3b8d9dee4814402e974017aa9a0c9939
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585886B2

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