HCID 23467205, compound → HCID 23467217, compound

HRID 443423Notes

Reaction equation

HRID 443423 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]3[CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.C(O)(=O)C.[Pd]>[C:22]1([CH:15]2[CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]3[C:11]3([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[O:14]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 2

HCID 23467205HCID 23467205, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23467217HCID 23467217, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 11 g of hexahydro-1'-benzyl-1-phenylspiro[3H-oxazolo[3,4-a]pyridine-3,4'-piperidine] in 95 ml of methanol and 5 ml of acetic acid is mixed with 1 g of 20% palladium on carbon and subjected to hydrogen pressure of about 50 p.s.i. After the theoretical amount of hydrogen is consumed, the reaction is stopped and the filtered solution is evaporated to dryness in vacuo. The residue is dissolved in methylene dichloride and stirred with excess dilute ammonium hydroxide solution to convert the acetate salt of hexahydro-1-phenylspiro[3H-oxazolo[3,4-a]pyridine-3,4'-piperidine] to the free base. The organic layer containing the aforementioned free base is separated, washed with a saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated to dryness in vacuo. The residue is recrystallized from ethyl acetate or methanol-water to obtain the pure free base of hexahydro-1-phenylspiro[3H-oxazolo[3,4-a]pyridine-3,4'-piperidine]; mp 169°-171° C.; yield 7 g.

Workup

  1. customAfter the theoretical amount of hydrogen is consumed
  2. customthe filtered solution is evaporated to dryness in vacuo
  3. dissolutionThe residue is dissolved in methylene dichloride
  4. additionThe organic layer containing the aforementioned free base
  5. customis separated
  6. washwashed with a saturated sodium bicarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness in vacuo
  9. customThe residue is recrystallized from ethyl acetate or methanol-water

Sources & evidence

ORD record
ord-9389f6117e6a47259d1735185c09884c
Source dataset
uspto-grants-1981_04
Patent number
US04260623

Reaction notes

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