D-Tartaric acid → HCID 57889970, compound

HRID 1820233Notes

Reaction equation

HRID 1820233 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2(O)[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1.C(O)(=O)[C@H]([C@@H](C(O)=O)O)O>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH3:15])([CH3:14])[CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 439655D-Tartaric acidHCID 66759036HCID 66759036, compound

Product 1

HCID 57889970HCID 57889970, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of (R)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol, D-(−)-Tartaric Acid (6.2 g, 15.90 mmol) in concentrated hydrochloric acid (150 mL) was refluxed for 27 hours, during which time a clear solution was observed. The solution was cooled to 0° C., which caused a white solid to precipitate, and the pH was adjusted to ˜13 with the slow, careful addition of solid sodium hydroxide. The aqueous was extracted with EtOAc (3×300 mL), the combined organic layers were washed with 1N NaOH (3×100 mL), once with brine (100 mL), then dried over sodium sulfate and concentrated in-vacuo to yield the title compound (3.46 g, 15.60 mmol, 98% yield) as a pale yellow oil. MS (ESI+)=222/224, (M+H)+.

Workup

  1. temperaturewas refluxed for 27 hours, during which time a clear solution
  2. customto precipitate
  3. additioncareful addition of solid sodium hydroxide
  4. extractionThe aqueous was extracted with EtOAc (3×300 mL)
  5. washthe combined organic layers were washed with 1N NaOH (3×100 mL), once with brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-0ec0218068fd46e294d817fe4ead5518
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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