Hydrochloric Acid → HCID 66719276, compound

HRID 2369110Notes

Reaction equation

HRID 2369110 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C@@H:7]([C:12]([OH:14])=[O:13])[NH:8][CH2:9]2)=[CH:4][CH:3]=1.[ClH:15].[CH3:16]O>>[ClH:15].[CH3:16][O:13][C:12]([C@@H:7]1[CH2:6][C:5]2[C:10](=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)[CH2:9][NH:8]1)=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2733173L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 66719276HCID 66719276, compound

Procedure

To a suspension of (S)-7-hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid dehydrate (109 mmol) in methanol (150 mL) was added hydrochloric acid (27 mL of 4M solution in dioxane.) at r.t and the reaction mixture was refluxed for 4 h. The mixture was concentrated, resuspended in 150 mL of MeOH and hydrochloric acid (27 mL of 4M solution in dioxane.) added. The mixture refluxed for 4 h and was concentrated under reduced pressure. The residue was triturated with ether, filtered and washed with ether to give (S)-7-hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester hydrochloride salt (25.1 g). 1H NMR (400 MHz, DMSO d6): 10.1 (m, 2H), 9.62 (s, 1H), 7.03 (d, 1H), 6.7 (m, 1H), 6.26 (d, 1H), 4.48 (m, 1H), 4.21 (s, 2H), 3.77 (s, 3H), 3.17-2.96 (m, 2H).

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. concentrationThe mixture was concentrated
  3. additionhydrochloric acid (27 mL of 4M solution in dioxane.) added
  4. temperatureThe mixture refluxed for 4 h
  5. concentrationwas concentrated under reduced pressure
  6. customThe residue was triturated with ether
  7. filtrationfiltered
  8. washwashed with ether

Sources & evidence

ORD record
ord-693be930569045199a6fe67d195e14c9
Source dataset
uspto-grants-2014_04
Patent number
US08703766B2

Reaction notes

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