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

HRID 340880노트

반응식

HRID 340880 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc82baa8535e4af0abd1b5c6d16303c5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895582B2

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