4-Methylmorpholine → (S)-1,3'-Bipyrrolidin-1'-YL(4-fluorophenyl)methanone

HRID 1176064ノート

反応式

HRID 1176064 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN1CCOCC1.[N:18]1([C@H:23]2[CH2:27][CH2:26][NH:25][CH2:24]2)[CH2:22][CH2:21][CH2:20][CH2:19]1>ClC(Cl)C.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:25]2[CH2:26][CH2:27][C@H:23]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:24]2)=[O:8])=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 99734-Fluorobenzoic AcidHCID 7176274(3S)-3-(Pyrrolidin-1-YL)pyrrolidine

生成物 1

HCID 59725829(S)-1,3'-Bipyrrolidin-1'-YL(4-fluorophenyl)methanone収率 57%

試薬・触媒・溶媒 1

HCID 19746008DMF dichloroethane溶媒2 回

実験手順

A solution of 4-fluorobenzoic acid (1.5 g, 10.71 mmol) in dichloroethane:DMF (4:1) was treated with O-benzotriazol-1-yl-N,N,N′N′-tetramethlyuronium tetrafluoroborate (4.13 gm 12.85 mmol) and N-methylmorpholine (5.41 g, 53.55 mmol) followed by a solution of (3′S)-1,3′-bipyrrolidine (2.52 g, 11.77 mmol) in dichloroethane:DMF (4:1). The reaction mixture was stirred at room temperature for 3 h and quenched with saturated sodium hydrogen carbonate. The phases were separated. The aqueous phase was extracted with ethyl acetate. The organic phase and the extracts were combined, washed sequentially with water and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash column chromatography to provide (3′S)-1′-(4-fluorobenzoyl)-1,3′-bipyrrolidine (57%) as a white solid.

後処理

  1. customquenched with saturated sodium hydrogen carbonate
  2. customThe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washwashed sequentially with water and saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-6d6b8f2e0c0449b797e70ebed41c4fe4
出典データセット
uspto-grants-2010_11
特許番号
US07842715B2

反応ノート

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