(5S,1'S)-5-<(3'-ethoxy-5'-oxocyclohex-3'-en-1'-yl)methyl>-1-(phenylmethyl)pyrrolidin-2-one

Base Information

• Chemical Name: (5S,1'S)-5-<(3'-ethoxy-5'-oxocyclohex-3'-en-1'-yl)methyl>-1-(phenylmethyl)pyrrolidin-2-one
• CAS No.: 131879-92-0
• Molecular Formula: C₂₀H₂₅NO₃
• Molecular Weight: 327.423

Synonyms:(5S,1'S)-5-<(3'-ethoxy-5'-oxocyclohex-3'-en-1'-yl)methyl>-1-(phenylmethyl)pyrrolidin-2-one

Chemical Property of (5S,1'S)-5-<(3'-ethoxy-5'-oxocyclohex-3'-en-1'-yl)methyl>-1-(phenylmethyl)pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (5S,1'S)-5-<(3'-ethoxy-5'-oxocyclohex-3'-en-1'-yl)methyl>-1-(phenylmethyl)pyrrolidin-2-one

There total 12 articles about (5S,1'S)-5-<(3'-ethoxy-5'-oxocyclohex-3'-en-1'-yl)methyl>-1-(phenylmethyl)pyrrolidin-2-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: 25.0%

ethanol (64-17-5) + (S)-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>-1,3-cyclohexanedione (131879-91-9) → (5S,1'S)-5-<(3'-ethoxy-5'-oxocyclohex-3'-en-1'-yl)methyl>-1-(phenylmethyl)pyrrolidin-2-one (131879-92-0) + (5S,1S)-5-<(3-ethoxy-5-oxo-3-cyclohexen-1-yl)methyl>-1-(phenylmethyl)-2-pyrrolidinone (131879-93-1)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 1.5h;

DOI:10.1021/jm00015a009

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (5S,1'S)-5-<(3'-ethoxy-5'-oxocyclohex-3'-en-1'-yl)methyl>-1-(phenylmethyl)pyrrolidin-2-one (131879-92-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) NaBH₄, NaOH, 2.) 6N HCl / H₂O / 1.) from 10 to 15 deg C, 30 min, 2.) RT, overnight

2: 55 percent / aq. HCl / Heating

3: 132 g / conc. H₂SO₄ / toluene / Heating

4: 77 percent / NaBH₄, MeOH / 2-methyl-propan-2-ol / Ambient temperature

5: DMAP / CH₂Cl₂ / Ambient temperature

6: NaI / acetone / Heating

7: 66 percent / Li₂CuCl₄ / tetrahydrofuran / -78 °C

8: 84.4 percent / 1.) O₃, 2.) aq. Me₂S / methanol; CH₂Cl₂ / 6.5 h / -78 °C

9: 95.6 percent / toluene / 5.5 h / 90 °C

10: 1.) NaOEt, 2.) ethanolic KOH, 3.) aq. HCl

11: 25 percent / p-TsOH*H₂O / toluene / 1.5 h

With hydrogenchloride; methanol; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; dilithium tetrachlorocuprate; dimethylsulfide; sulfuric acid; sodium ethanolate; toluene-4-sulfonic acid; ozone; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jm00015a009

Reference yield:

(S)-(+)-2-benzylamino glutaric acid (77539-18-5,73914-82-6) → (5S,1'S)-5-<(3'-ethoxy-5'-oxocyclohex-3'-en-1'-yl)methyl>-1-(phenylmethyl)pyrrolidin-2-one (131879-92-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 55 percent / aq. HCl / Heating

2: 132 g / conc. H₂SO₄ / toluene / Heating

3: 77 percent / NaBH₄, MeOH / 2-methyl-propan-2-ol / Ambient temperature

4: DMAP / CH₂Cl₂ / Ambient temperature

5: NaI / acetone / Heating

6: 66 percent / Li₂CuCl₄ / tetrahydrofuran / -78 °C

7: 84.4 percent / 1.) O₃, 2.) aq. Me₂S / methanol; CH₂Cl₂ / 6.5 h / -78 °C

8: 95.6 percent / toluene / 5.5 h / 90 °C

9: 1.) NaOEt, 2.) ethanolic KOH, 3.) aq. HCl

10: 25 percent / p-TsOH*H₂O / toluene / 1.5 h

With hydrogenchloride; methanol; dmap; potassium hydroxide; sodium tetrahydroborate; dilithium tetrachlorocuprate; dimethylsulfide; sulfuric acid; sodium ethanolate; toluene-4-sulfonic acid; ozone; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jm00015a009

upstream raw materials:

ethanol

(S)-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>-1,3-cyclohexanedione

L-glutamic acid

(S)-(+)-2-benzylamino glutaric acid

Downstream raw materials:

(5S,1R)-5-<(3-methyl-5-oxo-3-cyclohexen-1-yl)methyl>-1-(phenylmethyl)-2-pyrrolidinone

(5S,1'R,5'S)-5-<<3'-oxo-5'-<<1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-imidazol-2-yl>methyl>cyclohex-1'-yl>methyl>-1-(phenylethyl)-pyrrolidin-2-one

(5S,1'R)-5-<5'-oxo<3'-<<1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-imidazol-2-yl>methyl>cyclohex-3'-en-1'-yl>methyl>-1-(phenylmethyl)pyrrolidin-2-one

(1RS,3S,5R,2S)-5-<(1H-imidazol-4-yl)methyl>-3-<<5'-oxo-1'-(phenylmethyl)pyrrolidin-2'-yl>methyl>cyclohexanecetamide

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