Trifluoroacetic acid → (3-(Benzyloxy)phenyl)methanamine

HRID 2080037Notes

Reaction equation

HRID 2080037 reaction equation
C(OC([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>>[CH2:24]([O:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][NH2:8])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67119574(3-Benzyloxybenzyl) iminodicarboxylic acid di-tert-butyl ester

Product 1

HCID 11009288(3-(Benzyloxy)phenyl)methanamineYield 82%

Procedure

Lastly, (3-benzyloxybenzyl)iminodicarboxylic acid di-tert-butyl ester (691 mg, 1.67 mmol) was cooled on an ice bath, trifluoroacetic acid (3 mL) was added, and the solution was stirred for 30 minutes. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution, which was then extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the title compound (292 mg, 82%) was obtained as a white waxy solid. This was used in the next reaction without further purification.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-70da7d0e957f42928bf9170b1b5bbef0
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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