(S)-(+)-N-(Boc)-2-methylpiperidine → HCID 12176154, compound

HRID 1747103Notes

Reaction equation

HRID 1747103 reaction equation
[C:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].I([O-])(=O)(=O)=[O:16].[Na+]>C(OCC)(=O)C.O.O.[Ru](=O)=O>[C:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][C:9]1=[O:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 2

HCID 11019870(S)-(+)-N-(Boc)-2-methylpiperidineHCID 23667635Sodium periodate

Product 1

HCID 12176154HCID 12176154, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ruthenium(IV) oxide hydrate (0.8 g, 0.006 mol) then a solution of N-BOC-6(S)-methyl-piperidine (4.00 g, 0.020 mol) in ethyl acetate (240 ml) were added to a solution of sodium periodate (21.36 g, 0.100 mole) in water (200 ml) and strongly stirred for 24 hours at room temperature under argon atmosphere. After separation the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic phases were dried with magnesium sulfate and then treated with activated carbon, giving a colorless solution that was evaporated on a rotavapor at 30° C. The residue (3.98 g) was purified by silicagel (125 g) column chromatography with cyclohexane-ethyl acetate (1-1, v/v), furnishing a product (2.50 g, 59% yield) which according to its 1H-NMR spectrum was pure enough for the next reaction step.

Workup

  1. customAfter separation the aqueous phase
  2. extractionwas extracted with ethyl acetate (3×100 ml)
  3. dry with materialThe combined organic phases were dried with magnesium sulfate
  4. additiontreated with activated carbon
  5. customgiving a colorless solution that
  6. customwas evaporated on a rotavapor at 30° C
  7. customThe residue (3.98 g) was purified by silicagel (125 g) column chromatography with cyclohexane-ethyl acetate (1-1

Sources & evidence

ORD record
ord-a0190b0be5604c1583bdb6e417bf05b1
Source dataset
uspto-grants-2015_10
Patent number
US09150558B2

Reaction notes

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