Hydrochloric Acid → rac-(3R,6R)-6-methylpiperidin-3-ol hydrochloride

HRID 1852749Notes

Reaction equation

HRID 1852749 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[ClH:9]>CO.O=[Pt]=O>[ClH:9].[CH3:1][C@@H:2]1[NH:7][CH2:6][C@@H:5]([OH:8])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 86681862rac-(3R,6R)-6-methylpiperidin-3-ol hydrochloride

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-methylpyridin-3-ol (20.0 g, 0.183 mol) in MeOH (200 mL) were added concentrated HCl (15.43 mL, 0.1850 mol) and PtO2 (2.40 g, 0.011 mol). The resulting mixture was heated to 70° C. at 50 PSI overnight. The reaction was filtered to remove the PtO2 and concentrated to a solid to provide ±trans-6-methylpiperidin-3-ol hydrochloride. The crude solid was taken on without further purification.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove the PtO2
  3. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-cbe8906f48dd43a498044a6c65a8af18
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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