methyl (1S*,4aS*,8aR*)-7-benzyl-4a,5,6,,7,8,8a-hexahydro-1-methyl-1H-pyrano<3,4-c>pyridine-4-carboxylate

Base Information

• Chemical Name: methyl (1S*,4aS*,8aR*)-7-benzyl-4a,5,6,,7,8,8a-hexahydro-1-methyl-1H-pyrano<3,4-c>pyridine-4-carboxylate
• CAS No.: 95712-49-5
• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 301.386
• Mol file: 95712-49-5.mol

Synonyms:

Chemical Property of methyl (1S*,4aS*,8aR*)-7-benzyl-4a,5,6,,7,8,8a-hexahydro-1-methyl-1H-pyrano<3,4-c>pyridine-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S*,4aS*,8aR*)-7-benzyl-4a,5,6,,7,8,8a-hexahydro-1-methyl-1H-pyrano<3,4-c>pyridine-4-carboxylate

There total 11 articles about methyl (1S*,4aS*,8aR*)-7-benzyl-4a,5,6,,7,8,8a-hexahydro-1-methyl-1H-pyrano<3,4-c>pyridine-4-carboxylate 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:

1-methoxymethyloxy-2-pentyn-5-ol (108275-12-3) → methyl (1S*,4aS*,8aR*)-7-benzyl-4a,5,6,,7,8,8a-hexahydro-1-methyl-1H-pyrano<3,4-c>pyridine-4-carboxylate (95712-49-5,108341-84-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / H₂ / 5 percent Pd/CaCO₃/PbO / ethyl acetate / 0.25 h / 2327.2 Torr

2: 90 percent / pyridine / CH₂Cl₂ / 12 h / -15 °C

3: 88 percent / NaI / dimethylsulfoxide / 20 h / Ambient temperature

4: 85 percent / Et₃N, ethylchloroformate / CH₂Cl₂ / 6.5 h / Ambient temperature

5: 95 percent / H₂SO₄ / ethanol / 9 h / Heating

6: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

7: CH₂Cl₂ / 11 h / Heating

8: 73 percent / xylene / 18 h / 190 °C

9: 90 percent / AlH₃ / tetrahydrofuran / 1 h / Ambient temperature

10: neat (no solvent) / 2.5 h / 68 °C

11: Et₃N / 1.5 h / 56 °C

With pyridine; aluminium hydride; oxalyl dichloride; sulfuric acid; hydrogen; chloroformic acid ethyl ester; dimethyl sulfoxide; triethylamine; sodium iodide; Lindlar catalyst; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; xylene;

DOI:10.1016/S0040-4020(01)90579-4

Reference yield:

1-methoxymethyloxypent-2(Z)-ene-5-ol (95712-41-7) → methyl (1S*,4aS*,8aR*)-7-benzyl-4a,5,6,,7,8,8a-hexahydro-1-methyl-1H-pyrano<3,4-c>pyridine-4-carboxylate (95712-49-5,108341-84-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / pyridine / CH₂Cl₂ / 12 h / -15 °C

2: 88 percent / NaI / dimethylsulfoxide / 20 h / Ambient temperature

3: 85 percent / Et₃N, ethylchloroformate / CH₂Cl₂ / 6.5 h / Ambient temperature

4: 95 percent / H₂SO₄ / ethanol / 9 h / Heating

5: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

6: CH₂Cl₂ / 11 h / Heating

7: 73 percent / xylene / 18 h / 190 °C

8: 90 percent / AlH₃ / tetrahydrofuran / 1 h / Ambient temperature

9: neat (no solvent) / 2.5 h / 68 °C

10: Et₃N / 1.5 h / 56 °C

With pyridine; aluminium hydride; oxalyl dichloride; sulfuric acid; chloroformic acid ethyl ester; dimethyl sulfoxide; triethylamine; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; xylene;

DOI:10.1016/S0040-4020(01)90579-4

Reference yield:

N-benzyl-N-(5-(methoxymethoxy)pent-3(Z)-enyl)amine (95712-43-9) → methyl (1S*,4aS*,8aR*)-7-benzyl-4a,5,6,,7,8,8a-hexahydro-1-methyl-1H-pyrano<3,4-c>pyridine-4-carboxylate (95712-49-5,108341-84-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / Et₃N, ethylchloroformate / CH₂Cl₂ / 6.5 h / Ambient temperature

2: 95 percent / H₂SO₄ / ethanol / 9 h / Heating

3: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

4: CH₂Cl₂ / 11 h / Heating

5: 73 percent / xylene / 18 h / 190 °C

6: 90 percent / AlH₃ / tetrahydrofuran / 1 h / Ambient temperature

7: neat (no solvent) / 2.5 h / 68 °C

8: Et₃N / 1.5 h / 56 °C

With aluminium hydride; oxalyl dichloride; sulfuric acid; chloroformic acid ethyl ester; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; xylene;

DOI:10.1016/S0040-4020(01)90579-4

upstream raw materials:

methanol

1-methoxymethyloxypent-2(Z)-ene-5-ol

N-benzyl-N-(5-(methoxymethoxy)pent-3(Z)-enyl)amine

N-benzyl-N-crotonamide