Sodium Hydroxide → HCID 21107198, compound

HRID 2377375Notes

Reaction equation

HRID 2377375 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH:11]([N:15]([CH:17]3[CH2:19][CH2:18]3)[CH3:16])[CH2:10][CH2:9][C:8]([CH3:21])([CH3:20])[C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CO.O1CCCC1>[CH:17]1([N:15]([CH3:16])[CH:11]2[CH2:10][CH2:9][C:8]([CH3:20])([CH3:21])[C:7]3[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[CH:13][C:12]2=3)[CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57424234HCID 57424234, compound2×

Product 1

HCID 21107198HCID 21107198, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester (Intermediate 55, 0.236 g, 0.83 mmol) in methanol (4 mL) and tetrahydrofuran (4 mL) was treated with a 2M solution of sodium hydroxide (4 mL, 8 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo to a residue that was neutralized with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as a solid (0.22 g, 100%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo to a residue that
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-002f941e2f714947ba5ee649325da058
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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