D-Tartaric acid → HCID 86753649, compound

HRID 361603Notes

Reaction equation

HRID 361603 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][NH:8]1.[C:17]([OH:26])(=[O:25])[C@H:18]([C@@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19]>C(O)C>[OH:21][C@@H:20]([C@H:18]([OH:19])[C:17]([OH:26])=[O:25])[C:22]([OH:24])=[O:23].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][NH:8]1

Participants

4

Reactant 2

HCID 439655D-Tartaric acidHCID 4738526HCID 4738526, compound

Product 1

HCID 86753649HCID 86753649, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 22.2 g of (RS)-1-pyridin-2-yl-1,2,3,4-tetrahydro-isoquinoline in 500 ml of warm absolute ethanol was treated with 15.85 g of D-(-)-tartaric acid. After filtration of the slightly turbid solution, the clear solution obtained was left to stand at 20° C. for 6 h. and at 5° C. for a further 18 h. The precipitate formed was filtered off under suction and washed with absolute ethanol. A second crystallizate was obtained immediately from the mother liquor. The precipitates were combined (15.0 g, m.p. 155°-158° C.) and recrystallized from 900 ml of absolute ethanol. There were obtained 11.4 g of (R)-1-pyridin-2-yl-1,2,3,4-tetrahydro-isoquinoline (2S,3S)-2,3-dihydroxy-succinate (1:1) as a colorless product, m.p. 162°-165° C.

Workup

  1. filtrationAfter filtration of the slightly turbid solution
  2. customthe clear solution obtained
  3. waitwas left
  4. customThe precipitate formed
  5. filtrationwas filtered off under suction
  6. washwashed with absolute ethanol
  7. customA second crystallizate was obtained immediately from the mother liquor
  8. customrecrystallized from 900 ml of absolute ethanol

Sources & evidence

ORD record
ord-03887e2b50ba4cac97b9776d0e9be4fe
Source dataset
uspto-grants-1999_02
Patent number
US05866583

Reaction notes

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