Trifluoroacetic acid → (Benzyloxy)(methyl)amine

HRID 1397864Notes

Reaction equation

HRID 1397864 reaction equation
[CH2:1]([O:8][N:9](CC)[C:10](=O)OC(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][NH:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86675732Tert-butyl benzyloxy(ethyl)carbamate

Product 1

HCID 13417387(Benzyloxy)(methyl)amineYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

151 (616 mg) was dissolved in 4 ml of DCM and 4 ml of TFA was added then the reaction mixture was let 1 h at room temperature. The reaction mixture is concentrated and 50 ml of AcOEt are added. The organic phase are washed with saturated NaHCO3 and brine then dried over Na2SO4, filtered and concentrated to afford 152 as an oil (324 mg, 88%). 1H NMR (DMSO): δ 0.99 (t, 3H, J=7.3 Hz), 2.82 (m, 2H), 4.61 (s, 2H), 6.50 (t, 1H, J=5.8 Hz), 7.32 (m, 5H).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. addition50 ml of AcOEt are added
  3. washThe organic phase are washed with saturated NaHCO3 and brine
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2afd92299c0a479e8321d44082a83274
Source dataset
uspto-grants-2014_12
Patent number
US08901295B2

Reaction notes

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