Di-tert-butyl dicarbonate → Ethyl 5-[2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]-2-thiophenecarboxylate

HRID 1712936Notes

Reaction equation

HRID 1712936 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:10]=1)#[N:2].[O:19](C(OC(C)(C)C)=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O>CO.[Ni]>[C:23]([O:22][C:20]([NH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:10]=1)=[O:19])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 68705066Ethyl 5-(2-cyanophenyl)thiophene-2-carboxylate

Product 1

HCID 59463267Ethyl 5-[2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]-2-thiophenecarboxylateYield 86.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a slurry of ethyl 5-(2-cyanophenyl)thiophene-2-carboxylate (1.09 gm 4.24 mmol) in MeOH (8 mL) was added (BOC)2O (1.11 g, 5.08 mmol) and Raney Nickel (3.6 mL). The reaction mixture was allowed to stir at rt under an atmosphere of hydrogen overnight and then filtered through celite. The filtrate was concentrated and the residue was purified by column chromatography to give ethyl 5-(2-{[(tert-butoxycarbonyl)-amino]methyl}phenyl)thiophene-2-carboxylate (1.32 g, 86%).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b4400d6d0b4c41419b9e81927282f9f3
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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