Triethylamine → L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 339228Notes

Reaction equation

HRID 339228 reaction equation
[OH:1][C:2]1[C:11](I)=[C:10]2[C:5]([CH2:6][C@@H:7]([C:13]([OH:15])=[O:14])[NH:8][CH2:9]2)=[CH:4][C:3]=1I.CCN(CC)CC>O.[Pd]>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C@@H:7]([C:13]([OH:15])=[O:14])[NH:8][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 15928542HCID 15928542, compound

Product 1

HCID 2733173L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

(S)-7-Hydroxy-6,8-diiodo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (2.0 g, 4.5 mmol) and 5% Pd/C (0.48 g, 0.22 mmol) were suspended in H2O (24 mL) and Et3N (2.1 mL, 15 mmol). EtOH (73 mL) purged with H2 was then syringed into a reaction flask. The reaction mixture was topped with a balloon of H2 and stirred for 4 h. The reaction mixture was filtered through CELITE®, washing with MeOH, and concentrated in vacuo to give crude (S)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid which was used directly in the next step. MS (ESL) m/z 193.1 (M+H)+.

Workup

  1. customEtOH (73 mL) purged with H2
  2. customwas then syringed into a reaction flask
  3. filtrationThe reaction mixture was filtered through CELITE®
  4. washwashing with MeOH
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ba1d8c4ebb447aaba58261208424f56
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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