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

HRID 732640ノート

反応式

HRID 732640 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3b8d9dee4814402e974017aa9a0c9939
出典データセット
uspto-grants-2009_09
特許番号
US07585886B2

反応ノート

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