(+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone

Base Information

• Chemical Name: (+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone
• CAS No.: 614733-24-3
• Molecular Formula: C₂₀H₂₁NO₂
• Molecular Weight: 307.392
• Mol file: 614733-24-3.mol

Synonyms:(+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone

Chemical Property of (+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone

There total 11 articles about (+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone 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: 87.0%

benzyl bromide (100-39-0) + (+)-(5S,6S)-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone (614733-23-2) → (+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone (614733-24-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 2.16667h;

DOI:10.1016/S0040-4020(03)01063-9

Reference yield:

(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone (160237-99-0) → (+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone (614733-24-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 6 h / 20 °C

2: 68 percent / NaI; NaHCO₃ / dimethylformamide / 6 h / 60 - 70 °C

3: 92 percent / NaHCO₃; H₂ / Pd/C / ethanol / 2 h / 2585.74 Torr

4: 76 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

5: 93 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

6: 87 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

7: 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

8: methanol / 12 h / 20 °C

9: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

10: 4-(dimethylamino)pyridine / toluene / 1 h / Heating

11: 87 percent / NaH; Bu₄NI / tetrahydrofuran / 2.17 h / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(03)01063-9

Reference yield:

(-)-(3R,4S)-trans-3-benzyloxy-4-formyl-1-(p-methoxyphenyl)-2-azetidinone (160334-80-5) → (+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone (614733-24-3)

Guidance literature:

Multi-step reaction with 12 steps

1: NaBH₄ / tetrahydrofuran; H₂O / 0 - 20 °C

2: 100 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 6 h / 20 °C

3: 68 percent / NaI; NaHCO₃ / dimethylformamide / 6 h / 60 - 70 °C

4: 92 percent / NaHCO₃; H₂ / Pd/C / ethanol / 2 h / 2585.74 Torr

5: 76 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

6: 93 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

7: 87 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

8: 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

9: methanol / 12 h / 20 °C

10: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

11: 4-(dimethylamino)pyridine / toluene / 1 h / Heating

12: 87 percent / NaH; Bu₄NI / tetrahydrofuran / 2.17 h / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(03)01063-9

upstream raw materials:

benzyl bromide

(+)-(5S,6S)-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone

(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone

(-)-(3R,4S)-trans-3-benzyloxy-4-formyl-1-(p-methoxyphenyl)-2-azetidinone

Downstream raw materials:

(-)-(5S,6S)-1-benzyl-5-(benzyloxy)6-methyl-hexahydro-2-pyridinone