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

HRID 708563

Reaction equation

HRID 708563 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[CH2:8][NH:7][C@H:6]([C:13]([OH:15])=[O:14])[CH2:5]2.Cl.[CH3:17]O>>[CH3:17][O:14][C:13]([C@@H:6]1[CH2:5][C:4]2[C:9](=[CH:10][C:11]([OH:12])=[C:2]([OH:1])[CH:3]=2)[CH2:8][NH:7]1)=[O:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12926159(3S)-6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 6352721methyl (3S)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

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).

Workup

  1. customThe mixture was then evaporated
  2. washto wash all the solid material
  3. stirringStirring
  4. filtrationafter which the solid product was collected by filtration
  5. washwashed with 100 mL acetonitrile
  6. customdried under vacuum overnight

Sources & evidence

ORD record
ord-aaffa9a8d51849c59b9321d3b50dafda
Source dataset
uspto-grants-2015_11
Patent number
US09175003B2

Linked notes

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