L-Tartaric acid → L-Tartaric acid

HRID 1511849Notes

Reaction equation

HRID 1511849 reaction equation
[NH2:1][C@:2]1([C:21]([O:23][CH3:24])=[O:22])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:9][CH:8]=2)[CH2:3]1.[C:25]([OH:34])(=[O:33])[C@@H:26]([C@H:28]([C:30]([OH:32])=[O:31])[OH:29])[OH:27]>CO.[OH-].[OH-].[Pd+2]>[NH2:1][C@:2]1([C:21]([O:23][CH3:24])=[O:22])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:9][CH:8]=2)[CH2:3]1.[C:25]([OH:34])(=[O:33])[C@@H:26]([C@H:28]([C:30]([OH:32])=[O:31])[OH:29])[OH:27]

Participants

6

Reactant 2

HCID 444305L-Tartaric acidHCID 57554672(1R,3R)-methyl 1-amino-3-(4-(6-methoxyhex-1-ynyl)phenyl)cyclopentanecarboxylate

Product 2

HCID 444305L-Tartaric acidYield 100%HCID 57554704(1R,3R)-methyl 1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

To a slurry of palladium hydroxide on carbon (1.867 g, 2.66 mmol) in MeOH (250 mL) was added a solution of (1R,3R)-methyl 1-amino-3-(4-(6-methoxyhex-1-ynyl)phenyl)cyclopentanecarboxylate, L-tartaric Acid 2 (25.5 g, 53.2 mmol) in MeOH (50 mL). The reaction mixture was purged with hydrogen and an atmosphere of hydrogen was maintained via balloon. After about 15 hours the reaction mixture was filtered through Celite® and concentrated in vacuo to provide (1R,3R)-methyl 1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentanecarboxylate, L-tartaric acid 2 (25.6 g, 52.9 mmol, 100% yield) as a colorless solid.

Workup

  1. customThe reaction mixture was purged with hydrogen
  2. temperaturean atmosphere of hydrogen was maintained via balloon
  3. filtrationAfter about 15 hours the reaction mixture was filtered through Celite®
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4c3336a5e7949678e36927f39e790c4
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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