Hydrochloric Acid → 3,4-Piperidinediol, 1-butyl-5-(hydroxymethyl)-, (3R,4R,5R)-

HRID 1003377Notes

Reaction equation

HRID 1003377 reaction equation
C([O:8][C@H:9]1[C@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[CH2:12][N:11]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10]1)C1C=CC=CC=1.Cl>C(O)C.[Pd]>[CH2:18]([N:11]1[CH2:12][C@H:13]([CH2:16][OH:17])[C@@H:14]([OH:15])[C@H:9]([OH:8])[CH2:10]1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53945335(3R,4R,5R)-3-benzyloxy-1-butyl-5-hydroxymethyl-4-piperidinol

Product 1

HCID 101304273,4-Piperidinediol, 1-butyl-5-(hydroxymethyl)-, (3R,4R,5R)-Yield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3R,4R,5R)-3-Benzyloxy-1-(n-butyl)-5-hydroxymethyl-4-piperidinol (105 mg, 0.4 mmol) was dissolved in ethanol (20ml) containing aqueous hydrochloric acid (4N, 0.3 ml), and palladium on carbon (10%, 30mg) was added. The mixture was hydrogenated at 1 atm. H2 -pressure for 3h, filtered through celite and concentrated in vacuo. Purification on a silica gel column (Eluent: ethyl acetate/methanol/25% ammonium hydroxide (4/1/1%)) gave the free base of (3R,4R,5R)-1-butyl-5-hydroxymethyl-3,4-piperidinediol (Yield: 53 mg, 74%) as a semicrystalline compound.

Workup

  1. additionwas added
  2. filtrationH2 -pressure for 3h, filtered through celite and
  3. concentrationconcentrated in vacuo
  4. customPurification on a silica gel column (Eluent: ethyl acetate/methanol/25% ammonium hydroxide (4/1/1%))

Sources & evidence

ORD record
ord-943823cde65941a4856bd62cb1b9e0fe
Source dataset
uspto-grants-2000_04
Patent number
US06046214

Reaction notes

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