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Potassium Carbonate → (2S)-1-[N-(2-phenylhexahydro-2,5-methanopentalen-3a(1H)-yl)glycyl]pyrrolidine-2-carbonitrile

HRID 1015569
ノート
印刷プレビュー

反応式

HRID 1015569 の反応式
[C:1]1([C:7]23[CH2:15][CH:11]4[CH2:12][CH:13]([CH2:14]2)[C:9]([NH2:16])([CH2:10]4)[CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:24][C:25]([N:27]1[CH2:31][CH2:30][CH2:29][C@H:28]1[C:32]#[N:33])=[O:26]>CS(C)=O.CCOC(C)=O>[C:1]1([C:7]23[CH2:15][CH:11]4[CH2:10][C:9]([NH:16][CH2:24][C:25]([N:27]5[CH2:31][CH2:30][CH2:29][C@H:28]5[C:32]#[N:33])=[O:26])([CH2:8]2)[CH:13]([CH2:12]4)[CH2:14]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 11073883(2S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrileHCID 593749631-Phenyltricyclo[3.3.1.03,7]nonan-3-amine

生成物 1

HCID 24853441(2S)-1-[N-(2-phenylhexahydro-2,5-methanopentalen-3a(1H)-yl)glycyl]pyrrolidine-2-carbonitrile収率 48.7%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred mixture of the compound obtained from step II (0.2 g, 0.94 mmol) and K2CO3 (0.39 g, 2.8 mmol) in DMSO (4.0 mL) at ice bath temperature under nitrogen atmosphere (S)-1-(2-chloro-acetyl)pyrrolidine-2-carbonitrile (0.16 g, 0.94 mmol) was added. After stirring the reaction mixture for 3 h at r.t., it was diluted with EtOAc and washed with water and brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain (2S)-1-[N-(2-phenylhexahydro-2,5-methanopentalen-3a(1H)-yl)glycyl]pyrrolidine-2-carbonitrile as off-white solid (0.16 g) in 48% yield. m/z (M+1) 350; 1H NMR (CDCl3) 300 MHz δ 7.35-7.16 (m, 5H), 4.4.85-4.76 (m, 1H), 3.76-3.40 (m, 2H), 3.50 (s, 2H), 2.48-2.41 (m, 1H), 2.36-2.27 (m, 2H), 2.23-2.0 (m, 6H), 1.94-1.68 (m, 4H), 1.66-1.60 (m, 1H).

後処理

  1. additionwas added
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-c68461ffca414bf899641e1d4c970214
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07985759B2

反応ノート

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