Methanol → Methyl 6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

HRID 409742ノート

反応式

HRID 409742 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH:6]([C:12]([OH:14])=[O:13])[CH2:5]2.O=S(Cl)Cl.[CH3:19]O>>[CH3:19][O:13][C:12]([CH:6]1[CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[CH2:8][NH:7]1)=[O:14]

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 579479416-Fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

生成物 1

HCID 57947410Methyl 6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

実験手順

To a suspension of 6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in methanol (500 mL) was added SOCl2 (50 mL). The reaction mixture was then refluxed for 1 h until LC-MS indicated the completion of the reaction. The mixture was concentrated, and the resulting residue was dissolved in a mixture of EtOAc (1 L) and sat. sodium bicarbonate solution (500 mL). The organic layer was separated, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give 6-fluoro-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester as an oil (92 g). LRMS (M+H+) m/z 210.1.

後処理

  1. temperatureThe reaction mixture was then refluxed for 1 h until LC-MS
  2. customthe completion of the reaction
  3. concentrationThe mixture was concentrated
  4. dissolutionthe resulting residue was dissolved in a mixture of EtOAc (1 L) and sat. sodium bicarbonate solution (500 mL)
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-472e69e60d9545f7b1af2a7a845815b2
出典データセット
uspto-grants-2014_06
特許番号
US08759374B2

反応ノート

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