Trifluoroacetic acid → (2R)-1-Phenoxy-2-propanamine

HRID 911250Notes

Reaction equation

HRID 911250 reaction equation
C(OC([NH:8][C@@H:9]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:10])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:10][C@@H:9]([NH2:8])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10586857(R)-N-Boc-1-phenoxy-2-propanamine

Product 1

HCID 5324633(2R)-1-Phenoxy-2-propanamineYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve (R)-2-(tert-butoxycarbonylamino)-3-phenoxy-propane (340 mg, 1.35 mmol) in DCM (80 mL), add trifluoroacetic acid (35 mL), and stir at 0° C. for 2 h. Evaporate and purify by SCX chromatography to give the title compound as a colorless oil (186 mg, 91%). MS (ES+) m/z: 151 (M+H)+.

Workup

  1. customEvaporate
  2. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-ddad170496db43ab8c454e8464ed1a9e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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