Hydrochloric Acid → (3R,4R,5R)-5-(Hydroxymethyl)piperidine-3,4-diol hydrochloride

HRID 251524Notes

Reaction equation

HRID 251524 reaction equation
[CH2:1]1[NH:6][CH2:5][C@@H:4]([OH:7])[C@H:3]([OH:8])[C@H:2]1[CH2:9][OH:10].[ClH:11]>CO.C(O)(C)C.CC(C)=O>[CH2:1]1[NH:6][CH2:5][C@@H:4]([OH:7])[C@H:3]([OH:8])[C@H:2]1[CH2:9][OH:10].[ClH:11]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 447607Afegostat

Product 1

HCID 25105635(3R,4R,5R)-5-(Hydroxymethyl)piperidine-3,4-diol hydrochloride

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

Isofagomine free base (30 mg) was dissolved in MeOH (5 mL) and 4 N HCl (0.5 mL) in isopropanol and acetone (4.0 mL). The sample was stored refrigerated overnight and filtered. Crystals were observed in the solution. However, when filtered, the product was a yellow substance having a glue-like consistency.

Workup

  1. filtrationfiltered
  2. filtrationHowever, when filtered

Sources & evidence

ORD record
ord-9da3c37ffb3d419a9cd6da97cf8321b3
Source dataset
uspto-grants-2011_01
Patent number
US07863453B2

Reaction notes

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