methyl 4-[N-benzyl-N-(tert-butoxycarbonylmethyl)amino]cyclohex-1-enecarboxylate

Base Information

Chemical Name:methyl 4-[N-benzyl-N-(tert-butoxycarbonylmethyl)amino]cyclohex-1-enecarboxylate
CAS No.:422506-89-6
Molecular Formula:C₂₁H₂₉NO₄
Molecular Weight:359.466
Hs Code.:

Synonyms:methyl 4-[N-benzyl-N-(tert-butoxycarbonylmethyl)amino]cyclohex-1-enecarboxylate

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Chemical Property of methyl 4-[N-benzyl-N-(tert-butoxycarbonylmethyl)amino]cyclohex-1-enecarboxylate

Chemical Property:

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Technology Process of methyl 4-[N-benzyl-N-(tert-butoxycarbonylmethyl)amino]cyclohex-1-enecarboxylate

There total 5 articles about methyl 4-[N-benzyl-N-(tert-butoxycarbonylmethyl)amino]cyclohex-1-enecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

: 5292-43-3
bromoacetic acid tert-butyl ester

: 188562-99-4
methyl 4-benzylaminocyclohex-1-ene-1-carboxylate

: 422506-89-6
methyl 4-[N-benzyl-N-(tert-butoxycarbonylmethyl)amino]cyclohex-1-enecarboxylate

Guidance literature:: With sodium carbonate; In acetonitrile; for 24h; Heating;
DOI:10.1021/jo0163849

Reference yield:

: benzyl-(4-hydrazono-cyclohexyl)-carbamic acid tert-butyl ester

: 422506-89-6
methyl 4-[N-benzyl-N-(tert-butoxycarbonylmethyl)amino]cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 885 mg / I₂; 2-tetr-butyl-1,1,3,3-tetramethylguanidine / diethyl ether / 0 - 90 °C

2: 75 percent / PPh₃; DMPU; Et₃N / Pd(OAc)2 / 24 h / 55 °C

3: TFA / CH₂Cl₂ / 45 h / 20 °C

4: 85 percent / Na₂CO₃ / acetonitrile / 24 h / Heating

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine; sodium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium diacetate; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo0163849

Reference yield:

: 188562-91-6
tert-butyl N-benzyl(4-oxocyclohexyl)carbamate

: 422506-89-6
methyl 4-[N-benzyl-N-(tert-butoxycarbonylmethyl)amino]cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: hydrazine monohydrate; Et₃N / ethanol / 1.5 h / Heating

2: 885 mg / I₂; 2-tetr-butyl-1,1,3,3-tetramethylguanidine / diethyl ether / 0 - 90 °C

3: 75 percent / PPh₃; DMPU; Et₃N / Pd(OAc)2 / 24 h / 55 °C

4: TFA / CH₂Cl₂ / 45 h / 20 °C

5: 85 percent / Na₂CO₃ / acetonitrile / 24 h / Heating

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine; sodium carbonate; hydrazine hydrate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium diacetate; In diethyl ether; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jo0163849