(5S,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine

Base Information

Chemical Name:(5S,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine
CAS No.:547738-34-1
Molecular Formula:C₂₂H₃₃NO₂
Molecular Weight:343.51
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (5S,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine

Chemical Property:

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Technology Process of (5S,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine

There total 9 articles about (5S,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine 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:

: 85144-28-1
tert-butyl (2E)-hex-2-enoate

: 547738-34-1
(5S,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran / 1 h

1.2: 85 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: H₂ / 20 percent Pd/C / methanol / 12 h / 50 °C / 38000 Torr

3.1: 12.6 g / Et₃N / CH₂Cl₂ / 5 h / 20 °C

4.1: LDA / tetrahydrofuran / 2 h / -78 - -45 °C

4.2: 85 percent / tetrahydrofuran / -78 - 20 °C

5.1: LiAlH₄ / tetrahydrofuran / 12 h / Heating

6.1: 3.6 g / H₂ / 20 percent Pd(OH)2/C / methanol / 12 h / 50 °C / 38000 Torr

7.1: 88 percent / K₂CO₃ / acetonitrile; H₂O / 10 h / 50 °C

8.1: iodine; triphenylphosphine; imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

9.1: 410 mg / triethylamine / acetonitrile / 15 h / Heating

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; hydrogen; iodine; potassium carbonate; triethylamine; triphenylphosphine; lithium diisopropyl amide; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1.2: Michael addition / 7.1: Michael addition;
DOI:10.1021/jo0341261

Reference yield:

: 217823-13-7
tert-butyl (3R)-3-aminohexanoate

: 547738-34-1
(5S,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine

Guidance literature:: Multi-step reaction with 7 steps

1.1: 12.6 g / Et₃N / CH₂Cl₂ / 5 h / 20 °C

2.1: LDA / tetrahydrofuran / 2 h / -78 - -45 °C

2.2: 85 percent / tetrahydrofuran / -78 - 20 °C

3.1: LiAlH₄ / tetrahydrofuran / 12 h / Heating

4.1: 3.6 g / H₂ / 20 percent Pd(OH)2/C / methanol / 12 h / 50 °C / 38000 Torr

5.1: 88 percent / K₂CO₃ / acetonitrile; H₂O / 10 h / 50 °C

6.1: iodine; triphenylphosphine; imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

7.1: 410 mg / triethylamine / acetonitrile / 15 h / Heating

With 1H-imidazole; lithium aluminium tetrahydride; hydrogen; iodine; potassium carbonate; triethylamine; triphenylphosphine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 5.1: Michael addition;
DOI:10.1021/jo0341261

Reference yield:

: 217823-12-6
tert-butyl (3R)-3-aminohexanoate

: 547738-34-1
(5S,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine

Guidance literature:: Multi-step reaction with 8 steps

1.1: H₂ / 20 percent Pd/C / methanol / 12 h / 50 °C / 38000 Torr

2.1: 12.6 g / Et₃N / CH₂Cl₂ / 5 h / 20 °C

3.1: LDA / tetrahydrofuran / 2 h / -78 - -45 °C

3.2: 85 percent / tetrahydrofuran / -78 - 20 °C

4.1: LiAlH₄ / tetrahydrofuran / 12 h / Heating

5.1: 3.6 g / H₂ / 20 percent Pd(OH)2/C / methanol / 12 h / 50 °C / 38000 Torr

6.1: 88 percent / K₂CO₃ / acetonitrile; H₂O / 10 h / 50 °C

7.1: iodine; triphenylphosphine; imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

8.1: 410 mg / triethylamine / acetonitrile / 15 h / Heating

With 1H-imidazole; lithium aluminium tetrahydride; hydrogen; iodine; potassium carbonate; triethylamine; triphenylphosphine; lithium diisopropyl amide; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 6.1: Michael addition;
DOI:10.1021/jo0341261