Methanol → HCID 69014232, compound

HRID 1436487Notes

Reaction equation

HRID 1436487 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][C@H:5]([C:13]([OH:15])=[O:14])[NH:6][CH2:7]2.S(=O)(=O)(O)O.[CH3:21]O>>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][C@H:5]([C:13]([O:15][CH3:21])=[O:14])[NH:6][CH2:7]2

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 69014752HCID 69014752, compound

Product 1

HCID 69014232HCID 69014232, compoundYield 98%

Conditions

Temperature
85 °C

Procedure

Slurry the 5-bromo-8-hydroxy-1,2,3,4-tetrahydroisoquinoline-3(R)-carboxylic acid (1.538 g, 0.005652 mol) in methanol (60 mL). Add sulfuric acid (305 uL, 0.00572 mol). Heat at 85° C. for 2.5 days. Cool the solution to room temperature and concentrate under reduced pressure to a volume of ˜5 mL. Add ethyl acetate (100 mL) and neutralize with 10% aqueous potassium carbonate. Separate the layers and extract the aqueous layer with ethyl acetate (1×100 mL). Combine the organic layers and dry over magnesium sulfate. Concentrate the filtrate to give the desired product (1.65 g, 98%) as a light pink solid.

Workup

  1. temperatureCool the solution to room temperature
  2. concentrationconcentrate under reduced pressure to a volume of ˜5 mL
  3. customSeparate the layers
  4. extractionextract the aqueous layer with ethyl acetate (1×100 mL)
  5. dry with materialCombine the organic layers and dry over magnesium sulfate
  6. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-6fe6aedd285a4d4f929f0bf0668272fb
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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