(S)-tert-butyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate

Base Information

• Chemical Name: (S)-tert-butyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate
• CAS No.: 1352074-05-5
• Molecular Formula: C₂₈H₃₃Cl₂NO₃
• Molecular Weight: 502.481

Synonyms:(S)-tert-butyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate

Chemical Property of (S)-tert-butyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate

Chemical Property:

Purity/Quality:

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Technology Process of (S)-tert-butyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate

There total 11 articles about (S)-tert-butyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate 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:

C25H29Cl2NO3 (1352074-02-2) + allyl bromide (106-95-6) → (S)-tert-butyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate (1352074-05-5) + (S)-tert-butyl 2-((3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate (1352074-04-4)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 3h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jm300354j

Reference yield:

C19H20Cl2O5S → (S)-tert-butyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate (1352074-05-5) + (S)-tert-butyl 2-((3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate (1352074-04-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium azide / N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere

2.1: trimethylphosphane / tetrahydrofuran; water / 1 h / 25 °C / Inert atmosphere

3.1: sodium hydrogencarbonate / methanol; water / Inert atmosphere; Reflux

4.1: Chiralcel OD-H / hexane; isopropyl alcohol / Resolution of racemate

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C / Inert atmosphere

5.2: 24 h / 0 - 25 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With sodium azide; sodium hydride; sodium hydrogencarbonate; lithium hexamethyldisilazane; trimethylphosphane; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; isopropyl alcohol; mineral oil;

DOI:10.1021/jm300354j

Reference yield:

(+/-)-(4S,5R)-methyl 5-azido-4-(3-chlorophenyl)-5-(4-chlorophenyl)pentanoate → (S)-tert-butyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate (1352074-05-5) + (S)-tert-butyl 2-((3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate (1352074-04-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trimethylphosphane / tetrahydrofuran; water / 1 h / 25 °C / Inert atmosphere

2.1: sodium hydrogencarbonate / methanol; water / Inert atmosphere; Reflux

3.1: Chiralcel OD-H / hexane; isopropyl alcohol / Resolution of racemate

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C / Inert atmosphere

4.2: 24 h / 0 - 25 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With sodium hydride; sodium hydrogencarbonate; lithium hexamethyldisilazane; trimethylphosphane; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; isopropyl alcohol; mineral oil;

DOI:10.1021/jm300354j

upstream raw materials:

(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one

methyl 4-(3-chlorophenyl)-5-(4-chlorophenyl)-5-oxopentanoate

C₂₅H₂₉Cl₂NO₃

allyl bromide

Downstream raw materials:

(S)-tert-butyl 2-((3R,5R,6S)-3-(2-amino-2-oxo-ethyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)-butanoate

(S)-tert-butyl 2-((3R,5R,6S)-3-((1H-tetrazol-5-yl)methyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate

2-((3R,5R,6S)-1-((S)-1-(tert-butoxy)-1-oxo-butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-3-yl)acetic acid

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