2-tert-butyl 8a-methyl (8aR)-6-oxo-1,2,3,4,6,7,8,8a-octahydroisoquinoline-2,8a-dicarboxylate

Base Information

• Chemical Name: 2-tert-butyl 8a-methyl (8aR)-6-oxo-1,2,3,4,6,7,8,8a-octahydroisoquinoline-2,8a-dicarboxylate
• CAS No.: 445312-74-3
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• Mol file: 445312-74-3.mol

Synonyms:

Chemical Property of 2-tert-butyl 8a-methyl (8aR)-6-oxo-1,2,3,4,6,7,8,8a-octahydroisoquinoline-2,8a-dicarboxylate

Chemical Property:

• Boiling Point: 426.7±45.0 °C(Predicted)
• PKA: -2.73±0.40(Predicted)
• Density: 1.19±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(R)-2-tert-Butyl8a-methyl6-oxo-3,4,6,7,8,8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-tert-butyl 8a-methyl (8aR)-6-oxo-1,2,3,4,6,7,8,8a-octahydroisoquinoline-2,8a-dicarboxylate

There total 6 articles about 2-tert-butyl 8a-methyl (8aR)-6-oxo-1,2,3,4,6,7,8,8a-octahydroisoquinoline-2,8a-dicarboxylate 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: 70.0%

(+)-(S)-1-tert-butyl-3-methyl-4-oxo-3-(3-oxobutyl)piperidine-1,3-dicarboxylate (445312-71-0) → (R)-2-tert-butyl 8a-methyl 6-oxo-3,4,6,7,8, 8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate (445312-74-3,445312-78-7)

Guidance literature:

With pyrrolidine; acetic acid; In dichloromethane; at 23 ℃; for 16h;

DOI:10.1002/1099-0690(200205)2002:9<1505::AID-EJOC1505>3.0.CO;2-K

Reference yield:

N-(4-tert-butyloxycarbonyl-2-methoxycarbonyl-4-aza-1-cyclohexenyl)-L-valine diethylamide (445312-70-9) → (R)-2-tert-butyl 8a-methyl 6-oxo-3,4,6,7,8, 8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate (445312-74-3,445312-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Cu(OAc)2*H₂O / acetone / 16 h / 23 °C

2: pyridine; AcOH / CH₂Cl₂ / 16 h / 23 °C

With pyridine; copper diacetate; acetic acid; In dichloromethane; acetone; 1: Michael addition / 2: Robinson annulation;

DOI:10.1021/ol049831q

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-2-tert-butyl 8a-methyl 6-oxo-3,4,6,7,8, 8a-hexahydroisoquinoline-2,8a(1H)-dicarboxylate (445312-74-3,445312-78-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / K₂CO₃ / methanol / 16 h / 23 °C

2: 82 percent / 4 Angstroem molecular sieves / HCl / toluene / 16 h / 50 °C

3: Cu(OAc)2*H₂O / acetone / 16 h / 23 °C

4: HCl / H₂O / 2 h / 0 °C

5: 70 percent / pyrrolidine; AcOH / CH₂Cl₂ / 16 h / 23 °C

With pyrrolidine; hydrogenchloride; 4 A molecular sieve; potassium carbonate; acetic acid; hydrogenchloride; copper diacetate; In methanol; dichloromethane; water; acetone; toluene; 3: Michael reaction;

DOI:10.1002/1099-0690(200205)2002:9<1505::AID-EJOC1505>3.0.CO;2-K

upstream raw materials:

(+)-(S)-1-tert-butyl-3-methyl-4-oxo-3-(3-oxobutyl)piperidine-1,3-dicarboxylate

N-(4-tert-butyloxycarbonyl-2-methoxycarbonyl-4-aza-1-cyclohexenyl)-L-valine diethylamide

di-tert-butyl dicarbonate

methyl 4-oxo-3-piperidinecarboxylate hydrochloride