methyl (3S)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-6,7-Dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (62 g), 200 mL anhydrous MeOH, and 26 mL concentrated hydrochloric acid were stirred together overnight at 70° C. The mixture was then evaporated and the residue resuspended in 500 mL acetonitrile with vigorous stirring to wash all the solid material. Stirring continued for 18 h at r.t., after which the solid product was collected by filtration, washed with 100 mL acetonitrile, and dried under vacuum overnight. Yield 77 g (quantitative). 1H NMR (400 MHz, MeOH-d4): 6.64 (s, 1H), 6.61 (s, 1H), 4.42-4.36 (m, 1H), 4.29-4.24 (m, 2H), 3.89 (s, 3H), 3.29-3.22 (m, 1H), 3.11-3.02 (m, 1H). The mixture was then evaporated to wash all the solid material Stirring after which the solid product was collected by filtration washed with 100 mL acetonitrile dried under vacuum overnight

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-6,7-Dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (62 g), 200 mL anhydrous MeOH, and 26 mL concentrated hydrochloric acid were stirred together overnight at 70° C. The mixture was then evaporated and the residue resuspended in 500 mL acetonitrile with vigorous stirring to wash all the solid material. Stirring continued for 18 h at r.t., after which the solid product was collected by filtration, washed with 100 mL acetonitrile, and dried under vacuum overnight. Yield 77 g (quantitative). 1H NMR (400 MHz, MeOH-d4): 6.64(s, 1H), 6.61(s, 1H), 4.42-4.36(m, 1H), 4.29-4.24(m, 2H), 3.89(s, 3H), 3.29-3.22(m, 1H), 3.11-3.02(m, 1H). The mixture was then evaporated to wash all the solid material Stirring after which the solid product was collected by filtration washed with 100 mL acetonitrile dried under vacuum overnight

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-6,7-Dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (62 g), 200 mL anhydrous MeOH, and 26 mL concentrated hydrochloric acid were stirred together overnight at 70° C. The mixture was then evaporated and the residue resuspended in 500 mL acetonitrile with vigorous stirring to wash all the solid material. Stirring continued for 18 h at r.t., after which the solid product was collected by filtration, washed with 100 mL acetonitrile, and dried under vacuum overnight. Yield 77 g (quantitative). 1H NMR (400 MHz, MeOH-d4): 6.64(s, 1H), 6.61(s, 1H), 4.42-4.36(m, 1H), 4.29-4.24(m, 2H), 3.89(s, 3H), 3.29-3.22(m, 1H), 3.11-3.02(m, 1H). The mixture was then evaporated to wash all the solid material Stirring after which the solid product was collected by filtration washed with 100 mL acetonitrile dried under vacuum overnight

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-6,7-Dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (62 g), 200 mL anhydrous MeOH, and 26 mL concentrated hydrochloric acid were stirred together overnight at 70° C. The mixture was then evaporated and the residue resuspended in 500 mL acetonitrile with vigorous stirring to wash all the solid material. Stirring continued for 18 h at r.t., after which the solid product was collected by filtration, washed with 100 mL acetonitrile, and dried under vacuum overnight. Yield 77 g (quantitative). 1H NMR (400 MHz, MeOH-d4): 6.64 (s, 1H), 6.61 (s, 1H), 4.42-4.36 (m, 1H), 4.29-4.24 (m, 2H), 3.89 (s, 3H), 3.29-3.22 (m, 1H), 3.11-3.02 (m, 1H). The mixture was then evaporated to wash all the solid material Stirring after which the solid product was collected by filtration washed with 100 mL acetonitrile dried under vacuum overnight

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-6,7-Dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (62 g), 200 mL anhydrous MeOH, and 26 mL concentrated hydrochloric acid were stirred together overnight at 70° C. The mixture was then evaporated and the residue resuspended in 500 mL acetonitrile with vigorous stirring to wash all the solid material. Stirring continued for 18 h at r.t., after which the solid product was collected by filtration, washed with 100 mL acetonitrile, and dried under vacuum overnight. Yield 77 g (quantitative). 1H NMR (400 MHz, MeOH-d4): 6.64 (s, 1H), 6.61 (s, 1H), 4.42-4.36 (m, 1H), 4.29-4.24 (m, 2H), 3.89 (s, 3H), 3.29-3.22 (m, 1H), 3.11-3.02 (m, 1H). The mixture was then evaporated to wash all the solid material Stirring after which the solid product was collected by filtration washed with 100 mL acetonitrile dried under vacuum overnight

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-6,7-Dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (62 g), 200 mL anhydrous MeOH, and 26 mL concentrated hydrochloric acid were stirred together overnight at 70° C. The mixture was then evaporated and the residue resuspended in 500 mL acetonitrile with vigorous stirring to wash all the solid material. Stirring continued for 18 h at r.t., after which the solid product was collected by filtration, washed with 100 mL acetonitrile, and dried under vacuum overnight. Yield 77 g (quantitative). 1H NMR (400 MHz, MeOH-d4): 6.64(s, 1H), 6.61(s, 1H), 4.42-4.36(m, 1H), 4.29-4.24(m, 2H), 3.89(s, 3H), 3.29-3.22(m, 1H), 3.11-3.02(m, 1H). The mixture was then evaporated to wash all the solid material Stirring after which the solid product was collected by filtration washed with 100 mL acetonitrile dried under vacuum overnight

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-6,7-Dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (62 g), 200 mL anhydrous MeOH, and 26 mL concentrated hydrochloric acid were stirred together overnight at 70° C. The mixture was then evaporated and the residue resuspended in 500 mL acetonitrile with vigorous stirring to wash all the solid material. Stirring continued for 18 h at r.t., after which the solid product was collected by filtration, washed with 100 mL acetonitrile, and dried under vacuum overnight. Yield 77 g (quantitative). 1H NMR (400 MHz, MeOH-d4): 6.64 (s, 1H), 6.61 (s, 1H), 4.42-4.36 (m, 1H), 4.29-4.24 (m, 2H), 3.89 (s, 3H), 3.29-3.22 (m, 1H), 3.11-3.02 (m, 1H). The mixture was then evaporated to wash all the solid material Stirring after which the solid product was collected by filtration washed with 100 mL acetonitrile dried under vacuum overnight

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-6,7-Dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (62 g), 200 mL anhydrous MeOH, and 26 mL concentrated hydrochloric acid were stirred together overnight at 70° C. The mixture was then evaporated and the residue resuspended in 500 mL acetonitrile with vigorous stirring to wash all the solid material. Stirring continued for 18 h at r.t., after which the solid product was collected by filtration, washed with 100 mL acetonitrile, and dried under vacuum overnight. Yield 77 g (quantitative). 1H NMR (400 MHz, MeOH-d4): 6.64 (s, 1H), 6.61 (s, 1H), 4.42-4.36 (m, 1H), 4.29-4.24 (m, 2H), 3.89 (s, 3H), 3.29-3.22 (m, 1H), 3.11-3.02 (m, 1H). The mixture was then evaporated to wash all the solid material Stirring after which the solid product was collected by filtration washed with 100 mL acetonitrile dried under vacuum overnight