(1R*,3,4aS*,8aR*)-7-benzyl-3,4,4a,5,6,8a-hexahydro-3-methoxy-1-methyl-1H-pyrano<3,4-c>pyridin-8-(7H)-one

Base Information

• Chemical Name: (1R*,3,4aS*,8aR*)-7-benzyl-3,4,4a,5,6,8a-hexahydro-3-methoxy-1-methyl-1H-pyrano<3,4-c>pyridin-8-(7H)-one
• CAS No.: 108275-16-7
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• Mol file: 108275-16-7.mol

Synonyms:

Chemical Property of (1R*,3,4aS*,8aR*)-7-benzyl-3,4,4a,5,6,8a-hexahydro-3-methoxy-1-methyl-1H-pyrano<3,4-c>pyridin-8-(7H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R*,3,4aS*,8aR*)-7-benzyl-3,4,4a,5,6,8a-hexahydro-3-methoxy-1-methyl-1H-pyrano<3,4-c>pyridin-8-(7H)-one

There total 9 articles about (1R*,3,4aS*,8aR*)-7-benzyl-3,4,4a,5,6,8a-hexahydro-3-methoxy-1-methyl-1H-pyrano<3,4-c>pyridin-8-(7H)-one 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: 95.0%

methanol (67-56-1) + (1S*,4aR*,8aR*)-7-benzyl-1-methyl-4a,5,6,8a-tetrahydro-1H-pyrano<3,4-c>pyridin-8-(7H)-one (95712-47-3,95782-81-3) → (1R*,3,4aS*,8aR*)-7-benzyl-3,4,4a,5,6,8a-hexahydro-3-methoxy-1-methyl-1H-pyrano<3,4-c>pyridin-8-(7H)-one (108275-16-7,108341-85-1)

Guidance literature:

With perchloric acid; for 15h; Ambient temperature;

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

Reference yield:

1-methoxymethyloxy-2-pentyn-5-ol (108275-12-3) → (1R*,3,4aS*,8aR*)-7-benzyl-3,4,4a,5,6,8a-hexahydro-3-methoxy-1-methyl-1H-pyrano<3,4-c>pyridin-8-(7H)-one (108275-16-7,108341-85-1)

Guidance literature:

Multi-step reaction with 9 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: 95 percent / perchloric acid (70percent) / 15 h / Ambient temperature

With pyridine; perchloric acid; oxalyl dichloride; sulfuric acid; hydrogen; chloroformic acid ethyl ester; dimethyl sulfoxide; triethylamine; sodium iodide; Lindlar catalyst; In 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) → (1R*,3,4aS*,8aR*)-7-benzyl-3,4,4a,5,6,8a-hexahydro-3-methoxy-1-methyl-1H-pyrano<3,4-c>pyridin-8-(7H)-one (108275-16-7,108341-85-1)

Guidance literature:

Multi-step reaction with 8 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: 95 percent / perchloric acid (70percent) / 15 h / Ambient temperature

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

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

upstream raw materials:

methanol

(1S*,4aR*,8aR*)-7-benzyl-1-methyl-4a,5,6,8a-tetrahydro-1H-pyrano<3,4-c>pyridin-8-(7H)-one

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

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

Downstream raw materials:

(1R*,3R*,4R*)-N-benzyl-3<1'(S*)-hydroxyethyl>-4-<2-(1'',3''-dithiano)ethyl>piperidine-2-one

(4R*)-N-benzyl-3(E)-ethylideno-4-<2-(1',3'-dithiano)ethyl>piperidine-2-one