Sodium Hydroxide → 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid

HRID 2117036Notes

Reaction equation

HRID 2117036 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:19]3[CH2:25][CH:24]4[N:26]([CH3:27])[CH:21]([CH2:22][CH2:23]4)[CH2:20]3)[C:10]3[C:15]([O:16][C:17]=2[CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4].[OH-].[Na+]>C1COCC1>[CH3:27][N:26]1[CH:24]2[CH2:23][CH2:22][CH:21]1[CH2:20][CH:19]([N:9]1[C:8]3[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:18][C:17]=3[O:16][C:15]3[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:25]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5981467610-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid methyl ester2×

Product 1

HCID 5981473310-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acidYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid methyl ester, 2a (440 mg, 0.646 mmol) in THF (5 mL) was added 1N NaOH (5 mL), and the mixture was stirred for 3 hr at rt. The solvent was removed, the residue was dissolved in DMF and acidified with a 2N TFA solution, and purified via reverse phase HPLC to yield 295 mg (63%) of 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid, 3a, as a TFA salt. MS m/z (MH+) 351.1.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in DMF
  3. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-63b21a70297b46c89c8a7d43538c6d5c
Source dataset
uspto-grants-2008_10
Patent number
US07439239B2

Reaction notes

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