Methanol → Tartrate

HRID 429513

Reaction equation

HRID 429513 reaction equation
O.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[CH2:15][OH:16])=[CH:5][CH:4]=1.[C:17]([OH:26])(=[O:25])[C@@H:18]([C@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19].CO>C(O)(C)C>[C:22]([C@@H:20]([C@H:18]([C:17]([O-:26])=[O:25])[OH:19])[OH:21])([O-:24])=[O:23].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[CH2:15][OH:16])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 444305L-Tartaric acidHCID 69039254trans-(-)-4-(4-Fluorophenyl)-3-hydroxymethylpiperidine monohydrate

Product 2

HCID 119400TartrateYield 35.5%HCID 9855829(3S,4R)-4-(4-Fluorophenyl)-3-piperidinemethanolYield 35.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Subsequently, 10.00 g (44.0 mmol) of the trans-(−)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine monohydrate, 6.60 g (44.0 mmol) of L-tartaric acid, and 50 ml of methanol were mixed together, and 50 ml of isopropanol was added to the resulting mixture under ice-cooling. The mixture was allowed to stand to precipitate crystals, and the resulting crystals were filtered. The crystals were washed with a 10 ml mixed solvent of 5 ml of methanol and 5 ml of isopropanol and dried, to give 5.60 g (15.6 mmol) of L-tartrate of trans-(−)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine (yield: 35.5%).

Workup

  1. temperaturecooling
  2. customto precipitate crystals
  3. filtrationthe resulting crystals were filtered
  4. washThe crystals were washed with a 10 ml
  5. additionmixed solvent of 5 ml of methanol and 5 ml of isopropanol
  6. customdried

Sources & evidence

ORD record
ord-b163e41d8342420fa36e29a1adce8e7a
Source dataset
uspto-grants-2001_11
Patent number
US06316628B1

Linked notes

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