Hydrochloric Acid → Hydrochloric Acid

HRID 1873711Notes

Reaction equation

HRID 1873711 reaction equation
[ClH:1].C([N:9]1[CH2:14][C@H:13]([CH2:15][Cl:16])[C@@H:12]([OH:17])[C@H:11]([OH:18])[CH2:10]1)C1C=CC=CC=1>CCO>[Cl:16][CH2:15][C@H:13]1[CH2:14][NH:9][CH2:10][C@@H:11]([OH:18])[C@@H:12]1[OH:17].[ClH:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59533562HCID 59533562, compound

Product 2

HCID 313Hydrochloric AcidHCID 46918402HCID 46918402, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5N HCl (4.7 mmol, 0.94 mL) was added to (3R,4R,5S)-1-benzyl-5-(chloromethyl)piperidine-3,4-diol (3) (5.1 mmol, 1.3 g) dissolved in EtOH. Solution was evaporated in vacuo and then co-evaporated 2-3× with EtOH. The residue was redissolved in EtOH and combined with Pd(OH)2 (0.27 g), and hydrogenated at 55 psi for 12 hrs. The catalyst was subsequently filtered through dicalite and the filtrate was evaporated to obtain crude (4) as an HCl salt. This was then chromatographed (5-15% MeOH/NH4OH (9:1) in CHCl3) to give 0.4 g of (4) as a white solid with MH+ of 165 and 1H NMR (DMSO-d6) 1.6 (m, 1H), 2.2 (m, 3H), 2.9 (m, 3H), 3.15 (m, 1H), 3.6 (m, 1H), 3.8 (dd, 1H), 4.68 (d, 1H), 4.88 (d, 1H).

Workup

  1. customSolution was evaporated in vacuo
  2. dissolutionThe residue was redissolved in EtOH
  3. filtrationThe catalyst was subsequently filtered through dicalite
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-ce7fc3ad94af4f5ebda5a1293cf31145
Source dataset
uspto-grants-2012_11
Patent number
US08304429B2

Reaction notes

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