Sodium Hydroxide → HCID 13491118, compound

HRID 463707Notes

Reaction equation

HRID 463707 reaction equation
C[O:2][C:3]1(OC)[CH2:9][CH:8]2[C:4]1([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[CH2:5][NH:6][CH2:7]2.[OH-].[Na+]>Cl>[CH3:16][C:13]1[CH:12]=[CH:11][C:10]([C:4]23[C:3](=[O:2])[CH2:9][CH:8]2[CH2:7][NH:6][CH2:5]3)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13491117HCID 13491117, compound

Product 1

HCID 13491118HCID 13491118, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred mixture of about 4.1 g of 6,6-dimethoxy-5-(p-methyl-phenyl)-3-azabicyclo[3.2.0]heptane and about 50 ml of approximately 10% hydrochloric acid was heated under reflux for about 30 minutes. The solution was made basic with 5N sodium hydroxide and then was extracted with dichloromethane. The extract was dried over sodium sulfate, filtered, and evaporated under reduced pressure to give about 2.8 g of 5-(p-methylphenyl)-3-azabicyclo[3.2.0]heptane-6-one, b.p. 125°-130° C. (0.2 mm), as a yellow liquid. The fumarate salt had m.p. 130°-133° C. A mixture of about 3.8 g of the ketone, about 5 ml of 1,2-ethanedithiol and about 5 ml of freshly distilled boron trifluoride etherate in about 40 ml of acetic acid was stirred at room temperature for approximately 4 days, and then was evaporated under reduced pressure to give a tarry residue. This residue was slurried with ether and about 10% hydrochloric acid, and then the aqueous phase was made basic with approximately 5N sodium hydroxide and extracted with dichloromethane. The extract was dried over sodium sulfate and evaporated to give about 4.1 g of a solid. Recrystallization from acetonitrile gave 5-(p-methylphenyl)-3-methyl-spiro[3-azabicyclo[3.2.0]heptane-6,2'-[1,3]-dithiolane] as a tan solid, m.p. 81°-86° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for about 30 minutes
  3. extractionwas extracted with dichloromethane
  4. dry with materialThe extract was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d7a76ae9f7e348f289393fd164ee312c
Source dataset
uspto-grants-1985_10
Patent number
US04544665

Reaction notes

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