Ammonium formate → (2S,4S)-1-[[N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

HRID 227943ノート

反応式

HRID 227943 の反応式
C(OC([N:11]([CH2:28][C:29]([N:31]1[CH2:35][C@@H:34]([F:36])[CH2:33][C@H:32]1[C:37]#[N:38])=[O:30])[C:12]12[CH2:19][CH2:18][C:15]([C:20]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>CN(C)C=O.[C].[Pd]>[N:22]1([C:20]([C:15]23[CH2:14][CH2:13][C:12]([NH:11][CH2:28][C:29]([N:31]4[CH2:35][C@@H:34]([F:36])[CH2:33][C@H:32]4[C:37]#[N:38])=[O:30])([CH2:19][CH2:18]2)[CH2:17][CH2:16]3)=[O:21])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 68844891(2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

生成物 1

HCID 57756780(2S,4S)-1-[[N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile収率 88.7%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

(2S,4S)-1-[[N-Benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (20.0 mg) and 10% palladium carbon (12.0 mg) were dissolved in dimethylformamide (0.5 mL). While the solution was chilled in an ice bath, ammonium formate (43.1 mg) was added and the mixture was stirred for 40 minutes at the same temperature. Subsequently, the reaction mixture was filtered through a Celite pad and diluted with ethyl acetate. The organic layer washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluant:dichloromethane:methanol=10:1) to give (2S,4S)-1-[[N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (13.2 mg).

後処理

  1. temperatureWhile the solution was chilled in an ice bath
  2. filtrationSubsequently, the reaction mixture was filtered through a Celite pad
  3. additiondiluted with ethyl acetate
  4. washThe organic layer washed sequentially with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography (eluant:dichloromethane:methanol=10:1)

出典と根拠

ORDレコード
ord-5928b10f5afa4f4fa22ff4742e663e73
出典データセット
uspto-grants-2009_07
特許番号
US07560569B2

反応ノート

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