Trifluoroacetic acid → 6-Methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid

HRID 1994441Notes

Reaction equation

HRID 1994441 reaction equation
C(O)(C(F)(F)F)=O.C[O:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH:28]3[CH2:34][CH:33]4[N:35]([CH3:36])[CH:30]([CH2:31][CH2:32]4)[CH2:29]3)[C:17]3[C:22]([O:23][C:24]=2[CH:25]=1)=[C:21]([O:26][CH3:27])[CH:20]=[CH:19][CH:18]=3)=[O:11].[OH-].[Na+].COC(C1C=CC2N(C3CC4N(C)C(CC4)C3)C3C(OC=2C=1)=CC=CC=3)=O>O1CCOCC1>[CH3:27][O:26][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[O:23][C:24]1[CH:25]=[C:12]([C:10]([OH:11])=[O:9])[CH:13]=[CH:14][C:15]=1[N:16]2[CH:28]1[CH2:34][CH:33]2[N:35]([CH3:36])[CH:30]([CH2:31][CH2:32]2)[CH2:29]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 5981467610-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid methyl ester2×HCID 598146976-Methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid methyl ester2×

Product 1

HCID 598147056-Methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the TFA salt of 6-methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid methyl ester, 2e (270 mg, 0.7 mmol) in dioxane (15 mL) was added sodium hydroxide (31 mg, 0.77 mmol) for 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid methyl ester, 2a, the title compound 6-methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid, 3e was obtained as a mixture of endo and exo isomers. MS m/z (MH+) 381.

Sources & evidence

ORD record
ord-416ce21dfc3a4f50a0bb6fb80fc62fd1
Source dataset
uspto-grants-2010_01
Patent number
US07652005B2

Reaction notes

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