(2S)-cis-1-benzyl-2-(1-hydroxybutyl)-5-heptylpyrrolidine

Base Information

• Chemical Name: (2S)-cis-1-benzyl-2-(1-hydroxybutyl)-5-heptylpyrrolidine
• CAS No.: 95513-25-0
• Molecular Formula: C₂₂H₃₇NO
• Molecular Weight: 331.542
• Mol file: 95513-25-0.mol

Synonyms:

Chemical Property of (2S)-cis-1-benzyl-2-(1-hydroxybutyl)-5-heptylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-cis-1-benzyl-2-(1-hydroxybutyl)-5-heptylpyrrolidine

There total 17 articles about (2S)-cis-1-benzyl-2-(1-hydroxybutyl)-5-heptylpyrrolidine 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:

2-hydroxyoctanenitrile (66471-52-1) → (2S)-cis-1-benzyl-2-(1-hydroxybutyl)-5-heptylpyrrolidine (95513-25-0,95587-01-2,95587-07-8,95587-08-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 40percent H₂SO₄ / 3 h / 125 °C

2: 6 N NaOH

3: 83 percent / triethylamine / ethyl acetate / 7 h / Heating

4: 1.) pyridine / 1.) CH₂Cl₂, a) - 22 deg C, 15 min, b) 22 deg C, 15 min, 2.) RT, 1 h

5: acetonitrile / 1.) 0 deg C, 15 min, 2.) RT, 4 h

6: 1.) triphenyl phosphine, 2.) 1-methylpiperidine / 1.) CH₂Cl₂, 30 min, 2.) 0 deg C, 5 h

7: 86 percent / cyclohexene / 10percent Pd/C / methanol / 0.25 h / Heating

8: NaBH₄ / methanol / 0.5 h

9: K₂CO₃ / acetonitrile / 1.) 0 deg C, 30 min, 2.) RT, 16 h

10: 97 percent / AcOH, water / propan-1-ol / 6 h / Heating

11: diethyl ether / 1.) -78 deg C, 1 h, 2.) 0 deg C, 12 h

12: NaBH₄ / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 5 h

With pyridine; N-methylcyclohexylamine; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; water; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; cyclohexene; palladium on activated charcoal; In methanol; propan-1-ol; diethyl ether; ethanol; ethyl acetate; acetonitrile;

DOI:10.1021/jo00208a016

Reference yield:

2-hydroxy-octanoic acid (617-73-2) → (2S)-cis-1-benzyl-2-(1-hydroxybutyl)-5-heptylpyrrolidine (95513-25-0,95587-01-2,95587-07-8,95587-08-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 83 percent / triethylamine / ethyl acetate / 7 h / Heating

2: 1.) pyridine / 1.) CH₂Cl₂, a) - 22 deg C, 15 min, b) 22 deg C, 15 min, 2.) RT, 1 h

3: acetonitrile / 1.) 0 deg C, 15 min, 2.) RT, 4 h

4: 1.) triphenyl phosphine, 2.) 1-methylpiperidine / 1.) CH₂Cl₂, 30 min, 2.) 0 deg C, 5 h

5: 86 percent / cyclohexene / 10percent Pd/C / methanol / 0.25 h / Heating

6: NaBH₄ / methanol / 0.5 h

7: K₂CO₃ / acetonitrile / 1.) 0 deg C, 30 min, 2.) RT, 16 h

8: 97 percent / AcOH, water / propan-1-ol / 6 h / Heating

9: diethyl ether / 1.) -78 deg C, 1 h, 2.) 0 deg C, 12 h

10: NaBH₄ / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 5 h

With pyridine; N-methylcyclohexylamine; sodium tetrahydroborate; water; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; cyclohexene; palladium on activated charcoal; In methanol; propan-1-ol; diethyl ether; ethanol; ethyl acetate; acetonitrile;

DOI:10.1021/jo00208a016

Reference yield:

2-hydroxy-octanoic acid amide (28870-09-9) → (2S)-cis-1-benzyl-2-(1-hydroxybutyl)-5-heptylpyrrolidine (95513-25-0,95587-01-2,95587-07-8,95587-08-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 6 N NaOH

2: 83 percent / triethylamine / ethyl acetate / 7 h / Heating

3: 1.) pyridine / 1.) CH₂Cl₂, a) - 22 deg C, 15 min, b) 22 deg C, 15 min, 2.) RT, 1 h

4: acetonitrile / 1.) 0 deg C, 15 min, 2.) RT, 4 h

5: 1.) triphenyl phosphine, 2.) 1-methylpiperidine / 1.) CH₂Cl₂, 30 min, 2.) 0 deg C, 5 h

6: 86 percent / cyclohexene / 10percent Pd/C / methanol / 0.25 h / Heating

7: NaBH₄ / methanol / 0.5 h

8: K₂CO₃ / acetonitrile / 1.) 0 deg C, 30 min, 2.) RT, 16 h

9: 97 percent / AcOH, water / propan-1-ol / 6 h / Heating

10: diethyl ether / 1.) -78 deg C, 1 h, 2.) 0 deg C, 12 h

11: NaBH₄ / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 5 h

With pyridine; N-methylcyclohexylamine; sodium hydroxide; sodium tetrahydroborate; water; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; cyclohexene; palladium on activated charcoal; In methanol; propan-1-ol; diethyl ether; ethanol; ethyl acetate; acetonitrile;

DOI:10.1021/jo00208a016

upstream raw materials:

1-((2R,5S)-1-Benzyl-5-heptyl-pyrrolidin-2-yl)-butan-1-one

(5S)-1-benzyl-2-cyano-5-heptylpyrrolidine

(2R)-trans-1-benzyl-5-heptylproline

1-((2S,5S)-1-Benzyl-5-heptyl-pyrrolidin-2-yl)-butan-1-one

Downstream raw materials:

(+)-(S)-trans-2-heptyl-5-butylpyrrolidine

(+)-(S)-trans-2-heptyl-5-butyl-1-phenyl sulfonyl pyrrolidine

(2R)-trans-1-(phenylsulfonyl)-2-(1-<(phenylsulfonyl)oxy>butyl)-5-heptylpyrrolidine

cis-2-heptyl-5-butylpyrrolidine

Refernces