HCID 11780885, compound → HCID 131721277, compound

HRID 1415706Notes

Reaction equation

HRID 1415706 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[CH:10][C:9]=2[O:18][CH3:19])[C:4](=[O:20])[CH2:3]1.[C:21]([C@:29]([C:44]([OH:46])=[O:45])([OH:43])[C@:30]([C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([OH:34])[C:31]([OH:33])=[O:32])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[C:35]([C@:30]([C:31]([OH:33])=[O:32])([OH:34])[C@:29]([C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([OH:43])[C:44]([OH:46])=[O:45])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[CH3:1][N:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[CH:10][C:9]=2[O:18][CH3:19])[C:4](=[O:20])[CH2:3]1

Participants

4

Reactant 2

HCID 11780885HCID 11780885, compoundHCID 12362977Di-benzoyl-d-tartaric acid

Product 1

HCID 131721277HCID 131721277, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (±)-1-methyl-4-(2,4,6-trimethoxyphenyl)-3-piperidinone (1.60 g, 5.73 mmoles) and dibenzoyl-D-tartaric acid (2.28 g, 315 mmol) in 10 mL of methanol was heated at reflux temperature under argon atmosphere and it was cooled to room temperature. After stirring overnight at room temperature the precipitated solid was filtered, washed with a small amount of methanol to obtain the first crop of (R)-1-methyl-4-(2,4,6-trimethoxyphenyl)-3-piperidinone dibenzoyl-D-tartaric acid salt (2.65 g). The filtrate solution was concentrated to a volume of ca 6 mL and was stirred at ambient temperature for one day. The second crop of the chiral salt (0.24 g) was obtained by filtering the solid and washed it with a small amount of methanol.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature under argon atmosphere
  3. filtrationwas filtered
  4. washwashed with a small amount of methanol

Sources & evidence

ORD record
ord-9445d843b76f42ad8bfa7780195a4b8f
Source dataset
uspto-grants-1999_06
Patent number
US05908934

Reaction notes

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