[3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenyl]-carbamic acid tert-butyl ester
• CAS No.: 856011-05-7
• Molecular Formula: C₂₆H₃₆N₂O₂
• Molecular Weight: 408.584

Synonyms:[3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenyl]-carbamic acid tert-butyl ester

Chemical Property of [3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenyl]-carbamic acid tert-butyl ester

There total 6 articles about [3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenyl]-carbamic acid tert-butyl ester 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: 53.0%

tert-butyl alcohol (75-65-0) + 3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-benzoic acid (654648-03-0) → [3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenyl]-carbamic acid tert-butyl ester (856011-05-7)

Guidance literature:

With diphenyl-phosphinic acid; triethylamine; Heating;

DOI:10.1016/j.bmcl.2003.09.012

Reference yield:

phenylacetaldehyde (122-78-1) → [3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenyl]-carbamic acid tert-butyl ester (856011-05-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / BH₃; pyridine / ethanol / 25 °C

2: 67 percent / Et₃N / CH₂Cl₂ / 25 °C

3: 92 percent / Pd(OAc)2; DPPF; Et₃N / dimethylsulfoxide / 65 °C

4: 95 percent / aq. NaOH / tetrahydrofuran / Heating

5: 53 percent / DPPA; Et₃N / Heating

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium hydroxide; diphenyl-phosphinic acid; borane; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; 5: Curtius rearrangement;

DOI:10.1016/j.bmcl.2003.09.012

Reference yield:

3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol (119193-19-0) → [3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenyl]-carbamic acid tert-butyl ester (856011-05-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / BH₃; pyridine / ethanol / 25 °C

2: 67 percent / Et₃N / CH₂Cl₂ / 25 °C

3: 92 percent / Pd(OAc)2; DPPF; Et₃N / dimethylsulfoxide / 65 °C

4: 95 percent / aq. NaOH / tetrahydrofuran / Heating

5: 53 percent / DPPA; Et₃N / Heating

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium hydroxide; diphenyl-phosphinic acid; borane; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; 5: Curtius rearrangement;

DOI:10.1016/j.bmcl.2003.09.012

upstream raw materials:

tert-butyl alcohol

3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-benzoic acid

phenylacetaldehyde

3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol

Downstream raw materials:

3-((3R,4R)-3,4-Dimethyl-1-phenethyl-piperidin-4-yl)-phenylamine

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