Tert-butyl 4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenylcarbamate → 4-[3-(4-Fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylaniline

HRID 392891Notes

Reaction equation

HRID 392891 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:27]=[CH:28][C:29]=2[O:30][CH3:31])[CH2:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([NH:18]C(=O)OC(C)(C)C)=[CH:13][C:12]=2[CH3:26])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.ClCCl>[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:27]=[CH:28][C:29]=2[O:30][CH3:31])[CH2:10][C:11]2[C:12]([CH3:26])=[CH:13][C:14]([NH2:18])=[CH:15][C:16]=2[CH3:17])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 22662123Tert-butyl 4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenylcarbamate

Product 1

HCID 155521874-[3-(4-Fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylanilineYield 61.2%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

460 mg (1.02 mmol) of tert-butyl 4-[3-(4-fluorobenzyl)-4-methokybenzyl]-3,5-dimethylphenylcarbarnate (Example IX) are stirred in 10 ml of trifluoroacetic acid/dichloromethane (10% strength solution) at room temperature overnight. After neutralization with NaHCO3 solution, the organic phase is separated, dried over sodium sulphate and concentrated in a rotary evaporator. Chromatography (cyclohexane/ethyl acetate=6:1) affords 218 mg (55%) of 4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylaniline.

Workup

  1. customAfter neutralization with NaHCO3 solution, the organic phase is separated
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-c1425fc4dcab486c9c4a194cc762fcea
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Reaction notes

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