Acetic Acid → Tert-butyl 4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenylcarbamate

HRID 392890Notes

Reaction equation

HRID 392890 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:15](O)[C:16]3[C:21]([CH3:22])=[CH:20][C:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:18][C:17]=3[CH3:31])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])=[CH:4][CH:3]=1.C(O)(=O)C.[H][H]>CO.[Pd].[C]>[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[CH:18][C:17]=2[CH3:31])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 22662121HCID 22662121, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22662123Tert-butyl 4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenylcarbamateYield 78.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

590 mg of tert-butyl 4-[[3-(4-fluorobenzyl)-4-methoxyphenyl](hydroxy)methyl]-3,5-dimethylphenylcarbamate (Example VIII), 24 mg of Pd/carbon (10%) and a drop of acetic acid are hydrogenated in 10 ml of methanol with hydrogen at atmospheric pressure for 4 h. The suspension is filtered through kieselguhr. The filtrate is concentrated in a rotary evaporator. Chromatography (cyclohexane/ethyl acetate=6:1) affords 449 mg (77%) of tert-butyl 4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenylcarbamate.

Workup

  1. filtrationThe suspension is filtered through kieselguhr
  2. concentrationThe filtrate is concentrated in a rotary evaporator

Sources & evidence

ORD record
ord-38b3bcd2e6a148ca80dfda6b42f5b99e
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Reaction notes

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