Sodium Hydroxide → HCID 21107198, compound

HRID 1869895Notes

Reaction equation

HRID 1869895 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-tetrahydronaphthalene-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-90fe6c6673854f4aa6bfd611653b2674
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

Loading…