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

Base Information

• Chemical Name: (1R,3R,5S,5(2S))-3-methyl-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>cyclohexaneacetamide
• CAS No.: 131880-14-3
• Molecular Formula: C₂₁H₃₀N₂O₂
• Molecular Weight: 342.481

Synonyms:(1R,3R,5S,5(2S))-3-methyl-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>cyclohexaneacetamide

Chemical Property of (1R,3R,5S,5(2S))-3-methyl-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>cyclohexaneacetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,5S,5(2S))-3-methyl-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>cyclohexaneacetamide

There total 17 articles about (1R,3R,5S,5(2S))-3-methyl-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>cyclohexaneacetamide 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:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (1R,3R,5S,5(2S))-3-methyl-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>cyclohexaneacetamide (131880-14-3)

Guidance literature:

Multi-step reaction with 16 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

12: 52 percent / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

13: 1.) LDA / 1.) THF, from -40 to -50 deg C, 1 h, 2.) THF, from -50 to -20 deg C, 30 min

14: H₂ / 10percent Pd/C / ethanol / 5 h / 2585.7 Torr

15: KOH / ethanol / 0.5 h / Heating

16: 1.) EtOCOCl, Et₃N, 2.) NH₃(gas) / 1.) CHCl₃, from -30 to 0 deg C, 1 h, 2.) CHCl₃, 0 deg C, 1 h

With hydrogenchloride; methanol; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; dilithium tetrachlorocuprate; dimethylsulfide; sulfuric acid; ammonia; hydrogen; sodium ethanolate; chloroformic acid ethyl ester; toluene-4-sulfonic acid; ozone; triethylamine; sodium iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jm00015a009

Reference yield:

(S)-(+)-2-benzylamino glutaric acid (77539-18-5,73914-82-6) → (1R,3R,5S,5(2S))-3-methyl-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>cyclohexaneacetamide (131880-14-3)

Guidance literature:

Multi-step reaction with 15 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

11: 52 percent / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

12: 1.) LDA / 1.) THF, from -40 to -50 deg C, 1 h, 2.) THF, from -50 to -20 deg C, 30 min

13: H₂ / 10percent Pd/C / ethanol / 5 h / 2585.7 Torr

14: KOH / ethanol / 0.5 h / Heating

15: 1.) EtOCOCl, Et₃N, 2.) NH₃(gas) / 1.) CHCl₃, from -30 to 0 deg C, 1 h, 2.) CHCl₃, 0 deg C, 1 h

With hydrogenchloride; methanol; dmap; potassium hydroxide; sodium tetrahydroborate; dilithium tetrachlorocuprate; dimethylsulfide; sulfuric acid; ammonia; hydrogen; sodium ethanolate; chloroformic acid ethyl ester; toluene-4-sulfonic acid; ozone; triethylamine; sodium iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jm00015a009

Reference yield:

N-benzyl-L-pyroglutamic acid (38854-94-3,78964-11-1,7535-59-3) → (1R,3R,5S,5(2S))-3-methyl-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>cyclohexaneacetamide (131880-14-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 132 g / conc. H₂SO₄ / toluene / Heating

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

3: DMAP / CH₂Cl₂ / Ambient temperature

4: NaI / acetone / Heating

5: 66 percent / Li₂CuCl₄ / tetrahydrofuran / -78 °C

6: 84.4 percent / 1.) O₃, 2.) aq. Me₂S / methanol; CH₂Cl₂ / 6.5 h / -78 °C

7: 95.6 percent / toluene / 5.5 h / 90 °C

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

9: 25 percent / p-TsOH*H₂O / toluene / 1.5 h

10: 52 percent / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

11: 1.) LDA / 1.) THF, from -40 to -50 deg C, 1 h, 2.) THF, from -50 to -20 deg C, 30 min

12: H₂ / 10percent Pd/C / ethanol / 5 h / 2585.7 Torr

13: KOH / ethanol / 0.5 h / Heating

14: 1.) EtOCOCl, Et₃N, 2.) NH₃(gas) / 1.) CHCl₃, from -30 to 0 deg C, 1 h, 2.) CHCl₃, 0 deg C, 1 h

With hydrogenchloride; methanol; dmap; potassium hydroxide; sodium tetrahydroborate; dilithium tetrachlorocuprate; dimethylsulfide; sulfuric acid; ammonia; hydrogen; sodium ethanolate; chloroformic acid ethyl ester; toluene-4-sulfonic acid; ozone; triethylamine; sodium iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jm00015a009

upstream raw materials:

(1R,3R,5S,5(2S))-3-methyl-5-<<5-oxo-1-(phenylmethyl)-2-pyrrolidinyl>methyl>cyclohexaneacetic acid

L-glutamic acid

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

N-benzyl-L-pyroglutamic acid

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