Methanol → Methyl 6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
Reaction equation
[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]Participants
4
Procedure
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.
Workup
- temperatureThe reaction mixture was then refluxed for 1 h until LC-MS
- customthe completion of the reaction
- concentrationThe mixture was concentrated
- dissolutionthe resulting residue was dissolved in a mixture of EtOAc (1 L) and sat. sodium bicarbonate solution (500 mL)
- customThe organic layer was separated
- washwashed with water and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-472e69e60d9545f7b1af2a7a845815b2
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759374B2
Reaction notes
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