Hydrochloric Acid → (2R,3R,4R,5S)-1-(3-chloropropyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

HRID 1747015Notes

Reaction equation

HRID 1747015 reaction equation
C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[CH2:12][N:11]([CH2:31][CH2:32][CH2:33][Cl:34])[C@@H:10]1[CH2:35][O:36]CC1C=CC=CC=1)C1C=CC=CC=1.Cl>C(O)C.[Pd]>[Cl:34][CH2:33][CH2:32][CH2:31][N:11]1[CH2:12][C@H:13]([OH:23])[C@@H:14]([OH:15])[C@H:9]([OH:8])[C@H:10]1[CH2:35][OH:36]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118407745(2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-1-(3-chloropropyl)piperidine

Product 1

HCID 118407747(2R,3R,4R,5S)-1-(3-chloropropyl)-2-(hydroxymethyl)piperidine-3,4,5-triolYield 83.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of (2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-1-(3-chloropropyl)piperidine 4 (30 g, 49.98 mmol) in a mixture of ethanol (1.2 lit) and aqueous solution of HCl (1M, 100 mL) was added 10% Pd/C (3 g) and the mixture was degassed for 20 min using nitrogen. The reaction mixture was then stirred under 50 psi hydrogen pressure for 32 h. The reaction mixture was filtrate through celite, washed with ethanol (3×100 mL) and the filtrate was concentrated under reduced pressure to get crude hydrochloride salt of (2R,3R,4R,5S)-1-(3-chloropropyl)-2-(hydroxymethyl)piperidine-3,4,5-triol 5 (10 g, 83%) as black oil.

Workup

  1. customthe mixture was degassed for 20 min
  2. washwashed with ethanol (3×100 mL)
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-001b30e611214eb0910a4cbe20956f32
Source dataset
uspto-grants-2015_10
Patent number
US09150557B1

Reaction notes

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