Trifluoroacetic acid → 2-(Benzyloxy)ethanamine

HRID 911244Notes

Reaction equation

HRID 911244 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:11]([O:10][CH2:9][CH2:8][NH2:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21913792HCID 21913792, compound

Product 1

HCID 5338682-(Benzyloxy)ethanamineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve (2-benzyloxyethyl)-carbamic acid tert-butyl ester (15 g) in DCM (50 mL), add trifluoroacetic acid (20 mL) and stir at 0° C. for 3 h. Concentrate and dissolve the residue in a minimal amount of DCM. Purify by chromatography on silica gel eluting sequentially with hexane/EtOAc (4:1 and 1:1), EtOAc and 2M ammonia in methanol to give the title compound (8.3 g, 85%).

Workup

  1. concentrationConcentrate
  2. dissolutiondissolve the residue in a minimal amount of DCM
  3. customPurify by chromatography on silica gel eluting sequentially with hexane/EtOAc (4:1 and 1:1), EtOAc and 2M ammonia in methanol

Sources & evidence

ORD record
ord-f62abd5eac2c439aa3599c264dbeca43
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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