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

HRID 227943노트

반응식

HRID 227943 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

(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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5928b10f5afa4f4fa22ff4742e663e73
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560569B2

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