Hydrochloric Acid → (3S,4S)-3-Methyltetrahydro-2H-pyran-4-amine hydrochloride

HRID 905932Notes

Reaction equation

HRID 905932 reaction equation
C([NH:8][C@H:9]1[CH2:14][CH2:13][O:12][CH2:11][C@H:10]1[CH3:15])C1C=CC=CC=1.[ClH:16]>[OH-].[OH-].[Pd+2].CCO>[ClH:16].[CH3:15][C@H:10]1[C@@H:9]([NH2:8])[CH2:14][CH2:13][O:12][CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 121253854HCID 121253854, compound

Product 1

HCID 126970408(3S,4S)-3-Methyltetrahydro-2H-pyran-4-amine hydrochlorideYield 43%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Racemic cis benzyl-(3-methyl-tetrahydro-pyran-4-yl)-amine (1.8 g, 8.768 mmol) was dissolved in 3M HCl (4.4 mL, 13.2 mmol). Pd(OH)2 20 wt % (0.6 g) and EtOH (50 mL) were added and the reaction mixture was hydrogenated in a Parr shaker at 55 psi H2 over the weekend. The palladium was filtered off. HCl 4M in dioxane was added and the solvent was evaporated. The remaining green oil was adsorbed onto SiO2 and purified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100-55% DCM). The fractions containing the product were combined and HCl 4M in dioxane was added. NH4Cl crashed out. The solvent was evaporated. The remaining white semi-solid was taken up in MeOH/Et2O and the salt was filtered off and washed with Et2O. The filtrate was evaporated. The remaining oil was taken up in DCM and was evaporated again to obtain 0.58 of racemic cis 3-methyl-tetrahydro-pyran-4-ylamine hydrochloride as a light yellow solid (43% yield).

Workup

  1. filtrationThe palladium was filtered off
  2. additionHCl 4M in dioxane was added
  3. customthe solvent was evaporated
  4. custompurified by SiO2 chromatography (100 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100-55% DCM)
  5. additionThe fractions containing the product
  6. additionHCl 4M in dioxane was added
  7. customThe solvent was evaporated
  8. filtrationthe salt was filtered off
  9. washwashed with Et2O
  10. customThe filtrate was evaporated
  11. customwas evaporated again

Sources & evidence

ORD record
ord-42a3db9247f74582ba81105c79111363
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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